Benzocaine → Ethyl 4-[(5-phenylpentyl)amino]benzoate

HRID 1703091Notes

Reaction equation

HRID 1703091 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.[I-].[Na+].[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Cl)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C)P(N(C)C)(N(C)C)=O>C(O)C.O>[C:15]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][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:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 5238Sodium IodideHCID 12679HexamethylphosphoramideHCID 5191731-Chloro-5-phenylpentane

Product 1

HCID 13079663Ethyl 4-[(5-phenylpentyl)amino]benzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 18.2 g. of ethyl p-aminobenzoate 10.2 g. of sodium iodide, 10.0 g. of 5-phenylpentyl chloride and 60 ml. of hexamethylphosphoramide is stirred and heated at 110° C. in an oil bath for 20 hours. The mixture is chilled, diluted with 25 ml. of water and 25 ml. of ethanol, chilled and filtered. The solid is washed with 50 ml. of ethanol-water (1:1), with water and once with cold ethanol to give pale yellow crystals, m.p. 63°-64° C. Recrystallization from ethanol gives off-white crystals, m.p. 73°-75° C.

Workup

  1. additionA mixture of 18.2 g
  2. temperatureThe mixture is chilled
  3. additiondiluted with 25 ml
  4. filtrationfiltered
  5. washThe solid is washed with 50 ml
  6. customof ethanol-water (1:1), with water and once with cold ethanol to give pale yellow crystals, m.p. 63°-64° C
  7. customRecrystallization from ethanol
  8. customgives off-white crystals, m.p. 73°-75° C.

Sources & evidence

ORD record
ord-30facc8bb9254bca87b86558a68fd6b7
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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