Triethylamine → HCID 20071578, compound

HRID 981415Notes

Reaction equation

HRID 981415 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[CH2:23][C:24](O)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[CH2:23][C:24]([N:37]1[CH2:38][CH2:39][N:34]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:35][CH2:36]1)=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 76257Diethyl cyanophosphonateHCID 50283782-[2,4-Bis(benzyloxy)phenyl]acetic Acid

Product 1

HCID 20071578HCID 20071578, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To solution (15 ml) of 2,4-dibenzyloxyphenyl acetic acid (760 mg) and 1-benzylpiperazine (440 mg) in N,N-dimethylformamide are added triethylamine (0.6 ml) and diethyl cyanophosphate (420 mg) at 5° C. under stirring and stirring is continued for 15 minutes. To the reaction solution is added water and the product is extracted with dichloromethane. The dichloromethane layer is washed with water and dried. The solvent is distilled off to yield 1-(2,4-dibenzyloxyphenylacetyl)-4-benzylpiperazine (968 mg).

Workup

  1. stirringstirring
  2. extractionthe product is extracted with dichloromethane
  3. washThe dichloromethane layer is washed with water
  4. customdried
  5. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-ed42610e45004ab39ad07c5752f9dc22
Source dataset
uspto-grants-1991_02
Patent number
US04990511

Reaction notes

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