Triethylamine → 1-(2,4-Dibenzyloxyphenylacetyl)-4-benzylpiperidine

HRID 981411Notes

Reaction equation

HRID 981411 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[CH:24][C:23]=1[CH2:36][C:37](O)=[O:38])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C)C=O.O>[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[CH:24][C:23]=1[CH2:36][C:37]([N:11]1[CH2:12][CH2:13][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)=[O:38])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 317384-BenzylpiperidineHCID 76257Diethyl cyanophosphonateHCID 50283782-[2,4-Bis(benzyloxy)phenyl]acetic Acid

Product 1

HCID 544663701-(2,4-Dibenzyloxyphenylacetyl)-4-benzylpiperidineYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution (20 ml) of 4-benzylpiperidine (423 mg) and 2,4-dibenzyloxyphenylacetic acid (700 mg) in N,N-dimethylformamide are added triethylamine (0.56 ml) and diethyl cyanophosphate (393 mg) and the mixture is stirred at room temperature for 15 minutes. Water is added and stirring carried out for 10 minutes, followed by extraction of the product with dichloromethane. The dichloromethane layer is washed with water and dried over anhydrous sodium sulfate. The solvent is distilled off. The residue is subjected to purification by silica gel column chromatography. 1-(2,4-Dibenzyloxyphenylacetyl)-4-benzylpiperidine (1.0 g) in the colorless oily form is obtained from a fraction eluted with dichloromethane-ethyl acetate mixture (8:1).

Workup

  1. stirringstirring
  2. waitcarried out for 10 minutes
  3. extractionfollowed by extraction of the product with dichloromethane
  4. washThe dichloromethane layer is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is distilled off
  7. customThe residue is subjected to purification by silica gel column chromatography

Sources & evidence

ORD record
ord-3d4efafd76cb4adb96b74d8c1ab996f2
Source dataset
uspto-grants-1991_02
Patent number
US04990511

Reaction notes

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