Benzocaine → Ethyl 4-[(3-phenylpropyl)amino]benzoate

HRID 1703088Notes

Reaction equation

HRID 1703088 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.Br[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[C:17]1([CH2:16][CH2:15][CH2:14][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:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12503(3-Bromopropyl)benzeneHCID 12679Hexamethylphosphoramide

Product 1

HCID 13079659Ethyl 4-[(3-phenylpropyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33 g. of ethyl p-aminobenzoate, 19.9 g. of (3-bromopropyl)benzene and 80 ml. of hexamethylphosphoramide is heated at 110° C. for 20 hours. The mixture is chilled, diluted with 25 ml. of water, chilled, diluted with 50 ml. of ethanol and filtered. The solid is washed with cold ethanol-water (1:1) to give tan crystals, m.p. 80°-83° C. Two recrystallizations from ethanol give tan crystals, m.p. 87°-89° C.

Workup

  1. additionA mixture of 33 g
  2. temperatureThe mixture is chilled
  3. additiondiluted with 25 ml
  4. additiondiluted with 50 ml
  5. filtrationof ethanol and filtered
  6. washThe solid is washed with cold ethanol-water (1:1)
  7. customto give tan crystals, m.p. 80°-83° C
  8. customTwo recrystallizations from ethanol
  9. customgive tan crystals, m.p. 87°-89° C.

Sources & evidence

ORD record
ord-71787a14de9343468f66394a9bc4948c
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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