Benzocaine → Ethyl 4-[(8-phenyloctyl)amino]benzoate

HRID 2052498Notes

Reaction equation

HRID 2052498 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.CN(C)P(N(C)C)(N(C)C)=O.[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Cl)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[I-].[Na+]>C(O)C.O>[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][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:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 5238Sodium IodideHCID 12679HexamethylphosphoramideHCID 2901511-Chloro-8-phenyloctane

Product 1

HCID 13079665Ethyl 4-[(8-phenyloctyl)amino]benzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 14.9 g. of ethyl p-aminobenzoate, 50 ml. of hexamethylphosphoramide, 10.1 g. of 8-phenyloctyl chloride and 6.75 g. of sodium iodide is stirred and heated in an oil bath at 110° C. for 24 hours. The mixture is chilled, diluted with 50 ml. of water and 25 ml. of ethanol, chilled and filtered. The solid is washed with ethanol-water (1:1) and with water to give crystals, m.p. 61°-68° C. Recrystallization from ethanol gives white crystals, m.p. 75°-76° C.

Workup

  1. additionA mixture of 14.9 g
  2. temperatureThe mixture is chilled
  3. additiondiluted with 50 ml
  4. filtrationfiltered
  5. washThe solid is washed with ethanol-water (1:1) and with water
  6. customto give crystals, m.p. 61°-68° C
  7. customRecrystallization from ethanol
  8. customgives white crystals, m.p. 75°-76° C.

Sources & evidence

ORD record
ord-7b35f32039014e559a92d0d9e550a865
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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