Benzocaine → Ethyl 4-(15-carbomethoxypentadecylamino)benzoate

HRID 1278387Notes

Reaction equation

HRID 1278387 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][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].[NH2:21][C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1.CN(C)P(N(C)C)(N(C)C)=O>O>[C:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:31][CH:32]=1)([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 2736822Methyl 16-bromohexadecanoate

Product 1

HCID 21163354Ethyl 4-(15-carbomethoxypentadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 21 g. of methyl 16-bromohexadecanoate and 20 g. of ethyl 4-aminobenzoate in 150 ml. of hexamethylphosphoramide is stirred at 120° C. for 20 horus, cooled, diluted with water and filtered. A methylene chloride solution of the solid is dried over anhydrous magnesium sulfate, clarified with activated charcoal, and filtered through silica gel. The filtrate is evaporated and the residue crystallized from acetonitrile to yield ethyl 4-(15-carbomethoxypentadecylamino)benzoate as a white crystalline solid.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. dry with materialA methylene chloride solution of the solid is dried over anhydrous magnesium sulfate
  4. filtrationfiltered through silica gel
  5. customThe filtrate is evaporated
  6. customthe residue crystallized from acetonitrile

Sources & evidence

ORD record
ord-6ad2399f85db427fafd424bba8cdb596
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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