Benzocaine → Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

HRID 1703114Notes

Reaction equation

HRID 1703114 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.S(O[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(=O)(=O)C.CN(C)P(N(C)C)(N(C)C)=O.O1CCCC1>O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][CH2:18][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:22][CH:23]=1

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 8028TetrahydrofuranHCID 12679HexamethylphosphoramideHCID 130797053-(4-Chlorophenyl)propyl methanesulfonate

Product 1

HCID 13079692Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 49.5 g. of ethyl 4-aminobenzoate, 34.9 g. of 3-(p-chlorophenyl)propanol O-mesylate in 100 ml. of hexamethylphosphoramide is heated at 125°-130° C. for 16 hours. The solution is diluted with 50 ml. of tetrahydrofuran and with 150 ml. of water. Chilling and filtering gives crystals which are washed with water and recrystallized from ethanol to give 28.3 g. of light yellow crystals. Recrystallizations give the product as crystals, m.p. 122°-124° C.

Workup

  1. additionThe solution is diluted with 50 ml
  2. temperatureChilling
  3. filtrationfiltering
  4. customgives crystals which
  5. washare washed with water
  6. customrecrystallized from ethanol
  7. customto give 28.3 g
  8. customRecrystallizations

Sources & evidence

ORD record
ord-c88ca0b05d6b434e9ae586b57a0da707
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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