Benzocaine → HCID 768187, compound

HRID 2163349Notes

Reaction equation

HRID 2163349 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH:21]1C(C=O)=CC2OCOC=2[CH:22]=1.NC1C=CC(C(OCC)=O)=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[N:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([O:18][CH2:21][CH3:22])=[O:17])=[CH:14][CH:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 8438PiperonalHCID 521998p-Toluenesulfonic acid monohydrateHCID 7630164-[(1,3-Benzodioxol-5-ylmethyl)amino]benzoic acid

Product 1

HCID 768187HCID 768187, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Commercial quantities of 4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoic acid are generally prepared by reacting piperonal with ethyl 4-aminobenzoate in absolute ethanol in the presence of a catalytic amount of 4-toluenesulfonic acid monohydrate to give the intermediate ethyl 4-(((1,3-benzodioxol-5-yl)mehylene)amino)benzoate. The intermediate is isolated and reduced in absolute ethanol using sodium borohydrate. The resulting ethyl 4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoate is not isolated, but immediately hydrolyzed with aqueous sodium hydroxide to give sodium 4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoate. The salt is converted to 4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoic acid with aqueous acetic acid. The above process has been used to give satisfactory yields and was used to produce a batch containing 33 kg of pharmaceutically-acceptable product.

Sources & evidence

ORD record
ord-ac50117ad3f64c989f73a1f316d00e50
Source dataset
uspto-grants-1979_01
Patent number
US04133890

Reaction notes

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