Benzocaine → Ethyl 4-(11-hydroxyundecylamino)benzoate

HRID 1106142Notes

Reaction equation

HRID 1106142 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[NH2:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=1.C(N(CC)CC)C.CN(C)P(N(C)C)(N(C)C)=O>O>[OH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 8471TriethylamineHCID 12679HexamethylphosphoramideHCID 7416311-Bromo-1-undecanol

Product 1

HCID 20482494Ethyl 4-(11-hydroxyundecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 16 g. of 11-bromoundecanol, 9.9 g. of ethyl 4-aminobenzoate, and 6.0 g. of triethylamine in 50 ml. of hexamethylphosphoramide is stirred at 70° C. under argon for 128 hours. The resulting solution is cooled, diluted with water, and filtered. Recrystallization of the solid from acetonitrile affords ethyl 4-(11-hydroxyundecylamino)benzoate as a white, crystalline solid.

Workup

  1. temperatureThe resulting solution is cooled
  2. filtrationfiltered
  3. customRecrystallization of the solid from acetonitrile

Sources & evidence

ORD record
ord-f2b1b7c21714454a9b801cb9dbc0ce85
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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