Potassium Carbonate → HCID 21994100, compound

HRID 1978331Notes

Reaction equation

HRID 1978331 reaction equation
Br[CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[C:16]1([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:16]1([CH:22]2[CH2:23][CH2:24][N:25]([CH2:2][CH:3]3[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]3)[CH2:26][CH2:27]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

Product 1

HCID 21994100HCID 21994100, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.081 g (11.075 mM) of tert-butyl 4-(bromomethyl)piperidine-1-carboxylate, 1.96 g (12.2 mM) of 4-phenylpiperidine, and 3.06 g (22.2 mM) of potassium carbonate was stirred in 20 ml of N,N-dimethylformamide at 110° C. for 4 hours. This reaction mixture was poured in water and extracted with 2 portions of diethyl ether. The organic layers were combined and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to provide the title compound.

Workup

  1. extractionextracted with 2 portions of diethyl ether
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-c779747c36b34c1c888f71ec433f8fb1
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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