Benzocaine → Ethyl 4-{[2-(naphthalen-1-yl)ethyl]amino}benzoate

HRID 2052518Notes

Reaction equation

HRID 2052518 reaction equation
[C:1]1([CH2:11][CH2:12]Br)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[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>CN(C)P(N(C)C)(N(C)C)=O>[C:1]1([CH2:11][CH2:12][NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 1395411-(2-Bromoethyl)naphthalene

Product 1

HCID 44278897Ethyl 4-{[2-(naphthalen-1-yl)ethyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 4.7 g. of 2-(α-naphthyl)ethyl bromide and 6.6 g. of ethyl p-aminobenzoate in 50 ml. of hexamethylphosphoramide is stirred and heated at 110° C. for 16 hours. The mixture is cooled, diluted with 50 ml. of water and filtered to give a crude product, which is recrystallized from ethanol. Recrystallization gives ethyl 4-[2-(α-naphthyl)ethylamino]benzoate as white crystals, m.p. 104°-106° C.

Workup

  1. temperatureThe mixture is cooled
  2. additiondiluted with 50 ml
  3. filtrationof water and filtered
  4. customto give a crude product, which
  5. customis recrystallized from ethanol
  6. customRecrystallization

Sources & evidence

ORD record
ord-68212cdbbb6a4f9490e0ed3233742b24
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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