Benzocaine → Ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

HRID 1105890Notes

Reaction equation

HRID 1105890 reaction equation
[F:1][C:2]([F:20])([F:19])[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][CH2:17]Br.[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.C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[F:1][C:2]([F:20])([F:19])[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][CH2:17][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

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 1279729815-(Trifluoromethyl)pentadecyl bromide

Product 1

HCID 12797299Ethyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 18.5 g. of 15-(trifluoromethyl)pentadecyl bromide, 17.0 g. of ethyl 4-aminobenzoate, 7.1 g. of potassium carbonate, and 75 ml. of hexamethylphosphoramide is stirred for 16 hours at 120° C., allowed to cool, diluted with water, and filtered. The solid is dissolved in methylene chloride and the solution is dried over anhydrous magnesium sulfate and evaporated. The residual brown oil is crystallized from ethanol and recrystallized from acetonitrile to yield the product as a white solid.

Workup

  1. additionA mixture of 18.5 g
  2. temperatureto cool
  3. filtrationfiltered
  4. dissolutionThe solid is dissolved in methylene chloride
  5. dry with materialthe solution is dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residual brown oil is crystallized from ethanol
  8. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-c229e1fb1e96412dacf731444b164619
Source dataset
uspto-grants-1982_01
Patent number
US04310545

Reaction notes

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