Phenethyl bromide → HCID 86744623, compound

HRID 2372768Notes

Reaction equation

HRID 2372768 reaction equation
[C:1]1([N:7]([C@H:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[O:18][CH3:19])[C:8](=[O:11])[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1([CH2:26][CH2:27]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]1([N:7]([C@H:12]2[CH2:17][CH2:16][N:15]([CH:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:27])[CH2:14][C@H:13]2[O:18][CH3:19])[C:8](=[O:11])[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 67895978HCID 67895978, compound

Product 1

HCID 86744623HCID 86744623, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

cis-N-Phenyl-N-(3-methoxy-4-piperidinyl)propanamide (8, 0.5g, 1.9 mmol) from Example 6, phenylethyl bromide (0.40g, 2.2 mmol) and 2.76g (I9 mmol) of potassium carbonate in 100ml of acetonitrile were heated to reflux overnight. The reaction solution was concentrated under vacuum and the crude residue was purified by chromatography (silica gel; ethyl acetate) to yield 0.43g (62%, Rf 0.326) of pure cis-N-phenyl-N-(1-phenylethyl-3-methoxy-4-piperidinyl) propanamide (I).

Workup

  1. temperatureto reflux overnight
  2. concentrationThe reaction solution was concentrated under vacuum
  3. customthe crude residue was purified by chromatography (silica gel; ethyl acetate)

Sources & evidence

ORD record
ord-aba502456be841349dae3f445514d844
Source dataset
uspto-grants-1992_03
Patent number
US05100903

Reaction notes

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