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Preparation method of tetracaine hydrochloride

A tetracaine hydrochloride, preparation process technology, applied in the field of preparation of tetracaine hydrochloride, can solve problems such as difficult operation, need of reaction conditions, unsuitable for large-scale production, etc.

Inactive Publication Date: 2017-03-22
BEIJING VENTUREPHARM BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires reaction conditions of 1.5-2.0 Mpa hydrogen, is not easy to operate, and is not suitable for large-scale production

Method used

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  • Preparation method of tetracaine hydrochloride
  • Preparation method of tetracaine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: Preparation of 2-dimethylaminoethyl p-nitrobenzoate (4)

[0016] 5.0g (0.027mol) of p-nitrobenzoyl chloride (2), 2.4g (0.027mol) of dimethylaminoethanol (3), react in dichloromethane (50ml) at 0°C for 2h, add water (50ml ), separated, the organic layer was washed with saturated sodium bicarbonate solution (50 mL), separated, the organic layer was washed with saturated sodium bicarbonate solution (50 mL), dried, and concentrated to dryness to obtain 6.2 g of yellow oil, Yield 96.9%.

Embodiment 2

[0017] Embodiment 2: Preparation of p-aminobenzoic acid-2-dimethylaminoethyl ester (5)

[0018] Add 5.0g (0.021mol) of p-nitrobenzoic acid-2-dimethylaminoethyl ester (4), 1.8g (0.032mol) of iron powder, and 50mL of glacial acetic acid into a 100mL three-necked flask in sequence, start stirring, and heat up to 30°C , the reaction system was maintained at 30°C for 8 hours, then suction filtered, and saturated sodium carbonate solution was added to the filtrate until no bubbles were generated, then 20 mL of ethyl acetate was added for extraction, and the liquid was separated, and the aqueous phase was extracted with 20 mL of ethyl acetate, liquid separation, and combined The organic phase was spin-dried to obtain 3.5 g of a yellow solid with a yield of 72.9%.

Embodiment 3

[0019] Embodiment 3: the preparation of tetracaine (7)

[0020] 5.0g p-aminobenzoic acid-2-dimethylaminoethyl ester (5) (0.024mol), 3.3g 1-bromobutane (6) (0.024mol), 10.0g K 2 CO 3 (0.072mol) 50mL N,N-dimethylformamide was placed in a 100mL three-neck flask, started stirring, heated to 50°C, and the reaction system was maintained at 50°C for 5 hours, then stopped heating, the reaction system was cooled to room temperature, suction filtered, and the filtrate Add 50 mL of dichloromethane for extraction, separate the liquids, continue to extract the aqueous phase with 50 mL of dichloromethane, separate the liquids, combine the organic phases, and concentrate to dryness to obtain 5.3 g of white solids with a yield of 82.8%.

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Abstract

The invention relates to the technical field of preparation method of tetracaine hydrochloride. The preparation method comprises the preparation steps: carrying out a reaction of p-nitrobenzoyl chloride (2) and 2-dimethylamino-1-ethanol (3) to generate p-nitrobenzoic acid-2-dimethylamino ethyl (4), reducing the compound (3) to obtain p-aminobenzoic acid-2-dimethylamino ethyl (4), generating pontocaine (7) from a compound (5) and 1-bromobutane (6) under alkaline conditions, and finally carrying out a reaction of the pontocaine (7) with HCl to generate tetracaine hydrochloride (1).

Description

technical field [0001] The invention relates to the technical field of local anesthetics, in particular to a preparation method of tetracaine hydrochloride. Background technique [0002] Tetracaine hydrochloride is an ester local anesthetic. The local anesthetic effect is stronger than procaine, and the toxicity is also high. It can penetrate through the mucosa for epidural block, subarachnoid block, nerve conduction block, mucosal surface anaesthetization. After tetracaine hydrochloride enters the blood, most of it is combined with plasma protein and accumulates in tissues, and the accumulation amount is the largest in skeletal muscle. When the concentration in plasma decreases, it is released again. Most of tetracaine hydrochloride is produced by plasma choline It is hydrolyzed and transformed into p-aminobenzoic acid and dimethylaminoethanol through liver metabolism, and then degraded or combined and excreted with urine. [0003] Patent CN 10273133 A mentions a preparat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/18C07C229/60
CPCC07C213/06C07C227/04C07C227/18C07C229/60C07C219/14
Inventor 胡媛赵国磊
Owner BEIJING VENTUREPHARM BIOTECH
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