Benzocaine → Ethyl 4-[(7-phenylheptyl)amino]benzoate

HRID 1703095Notes

Reaction equation

HRID 1703095 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[I-].[Na+].CN(C)P(N(C)C)(N(C)C)=O>O.C(O)C.O>[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 5238Sodium IodideHCID 12679HexamethylphosphoramideHCID 5224107-Phenyl-1-heptyl chloride

Product 1

HCID 13079667Ethyl 4-[(7-phenylheptyl)amino]benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A mixture of 8.25 g. of ethyl p-aminobenzoate, 5.06 g. of 7-phenylheptylchloride, 3.6 g. of sodium iodide and 25 ml. of hexamethylphosphoramide is heated in an oil bath at 110° C. for 20 hours. The mixture is chilled, diluted with 30 ml. of ethanol-water (1:1) and with water to give crystals, m.p. 65°-67° C. Recrystallization from ethanol gives white crystals, m.p. 66.5°-68° C.

Workup

  1. additionA mixture of 8.25 g
  2. temperatureThe mixture is chilled
  3. additiondiluted with 30 ml
  4. customRecrystallization from ethanol
  5. customgives white crystals, m.p. 66.5°-68° C.

Sources & evidence

ORD record
ord-5553a517e07940cbaccf0a4a1c818145
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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