Triethylamine → HCID 54194718, compound

HRID 981409Notes

Reaction equation

HRID 981409 reaction equation
Cl.[F:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[C:17]([O:25][C:26]1[CH:31]=[C:30]([O:32][C:33](=O)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]=[CH:28][C:27]=1[CH2:41][C:42](O)=[O:43])(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C)C=O.O>[CH2:17]([O:25][C:26]1[CH:31]=[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]=[CH:28][C:27]=1[CH2:41][C:42]([N:12]1[CH2:13][CH2:14][CH:9]([C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([F:2])=[CH:16][CH:15]=2)[CH2:10][CH2:11]1)=[O:43])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 20071575HCID 20071575, compound

Product 1

HCID 54194718HCID 54194718, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To solution (20 ml) of 4-(4-fluorobenzoyl) piperidine. hydrochloride (670 mg) and 2,4-dibenzoyloxyphenylacetic acid (1.0 g) in N,N-dimethylformamide are added triethylamine (1.2 ml) and diethyl cyanophosphate (561 mg) and the mixture is stirred at room temperature for 10 minutes. To the reaction solution is added water and the mixture stirred for 20 minutes. The product is extracted with dichloromethane. The dichloromethane layer is washed with water and dried over anhydrous sodium sulfate, and then the solvent is distilled off. The residue is purified by silica gel column chromatography. The crude product is obtained from a fraction eluted with dichloromethane-ethyl acetate mixture (2:1). Recrystallization of the product from dichloromethane-diethyl ether mixture yields 1-(2,4-dibenzyloxyphenylacetyl)-4-(4-fluorobenzoyl)piperidine (1.25 g) in the colorless columnar crystal form. Melting point 158°-159° C.

Workup

  1. stirringthe mixture stirred for 20 minutes
  2. extractionThe product is extracted with dichloromethane
  3. washThe dichloromethane layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent is distilled off
  6. customThe residue is purified by silica gel column chromatography
  7. customThe crude product is obtained from a fraction
  8. washeluted with dichloromethane-ethyl acetate mixture (2:1)
  9. customRecrystallization of the product from dichloromethane-diethyl ether mixture

Sources & evidence

ORD record
ord-5b56074309184e2fb5edcabcedd8174a
Source dataset
uspto-grants-1991_02
Patent number
US04990511

Reaction notes

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