Water → Ethyl 4-({3-[4-(benzyloxy)phenyl]propyl}amino)benzoate

HRID 1703102Notes

Reaction equation

HRID 1703102 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)(=O)=O.CN(C)P(N(C)C)(N(C)C)=O.[NH2:34][C:35]1[CH:45]=[CH:44][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:37][CH:36]=1.O>C(O)C>[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][NH:34][C:35]2[CH:36]=[CH:37][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:44][CH:45]=2)=[CH:10][CH:11]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2337BenzocaineHCID 12679HexamethylphosphoramideHCID 13079701HCID 13079701, compound

Product 1

HCID 13079684Ethyl 4-({3-[4-(benzyloxy)phenyl]propyl}amino)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.8 g. of 3-[p-(benzyloxy)phenyl]propanol O-methanesulfonate (prepared as described in Example 43), 50 ml. of hexamethylphosphoramide and 16.5 g. of ethyl p-aminobenzoate is heated at 100°-105° C. for 17.5 hours. The mixture is chilled, diluted with 15 ml. of water, 30 ml. of ethanol and chilled. In order to filter, 100 ml. of ethanol-water (1:1) is added and the solid filtered and washed with ethanol-water (1:1) and with water to give tan crystals, m.p. 98°-107° C. Recrystallization from ethanol gives light tan crystals, m.p. 114°-116° C.

Workup

  1. additionA mixture of 12.8 g
  2. temperatureThe mixture is chilled
  3. additiondiluted with 15 ml
  4. filtrationIn order to filter
  5. additionof ethanol-water (1:1) is added
  6. filtrationthe solid filtered
  7. washwashed with ethanol-water (1:1) and with water
  8. customto give tan crystals, m.p. 98°-107° C
  9. customRecrystallization from ethanol
  10. customgives light tan crystals, m.p. 114°-116° C.

Sources & evidence

ORD record
ord-8c89aabd7c0d481396cb9b5d1f0b596e
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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