Phenethyl bromide → HCID 86744623, compound

HRID 981972Notes

Reaction equation

HRID 981972 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, 0.5 g, 1.9 mmol) from Example 6, phenylethyl bromide (0.40 g, 2.2 mmol) and 2.76 g (19 mmol) of potassium carbonate in 100 ml 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 0.43 g (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-6786e673fdf943df8df9d42bf5a525dd
Source dataset
uspto-grants-1991_02
Patent number
US04994471

Reaction notes

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