Benzocaine → Ethyl 4-[(6-phenylhexyl)amino]benzoate

HRID 2052510Notes

Reaction equation

HRID 2052510 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.CS(O[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)=O>CN(C)P(N(C)C)(N(C)C)=O>[C:24]1([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][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

4

Reactant 2

HCID 2337BenzocaineHCID 130797026-Phenylhex-1-yl methylsulfonate

Product 1

HCID 13079694Ethyl 4-[(6-phenylhexyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 34.9 g. of ethyl p-aminobenzoate, 26.9 g. of 6-phenylhexanol O-methanesulfonate (prepared as described in Example 47) and 200 ml. of hexamethylphosphoramide is heated at 110° C. in an oil bath for 20 hours. The mixture is cooled, diluted with 100 ml. of water and filtered. The solid is washed with 60 ml. of ethanol-water (1:1) to give crude ethyl 4-(6-phenylhexylamino)benzoate. Purification gives the product as crystals, m.p. 69.5°-72.5° C.

Workup

  1. temperatureThe mixture is cooled
  2. additiondiluted with 100 ml
  3. filtrationof water and filtered
  4. washThe solid is washed with 60 ml

Sources & evidence

ORD record
ord-11f74d07e5124dcb875c488b7f81cbe8
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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