Iodoethane → 4-(2-Bromo-5-ethoxybenzyl)-1-[(2-chlorophenyl)acetyl]piperidine

HRID 1006063Notes

Reaction equation

I[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[Br:10][C:11]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:12]=1[CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:29])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[CH2:16][CH2:15]1>CN(C)C=O>[Br:10][C:11]1[CH:33]=[CH:32][C:31]([O:34][CH2:2][CH3:3])=[CH:30][C:12]=1[CH2:13][CH:14]1[CH2:15][CH2:16][N:17]([C:20](=[O:29])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[CH2:18][CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

Iodoethane (311.9 mg, 2.000 mmol) and potassium carbonate (500.0 mg, 3.619 mmol) were added to a solution (3 ml) of 4-(2-bromo-5-hydroxybenzyl)-1-[(2-chlorophenyl)-acetyl]piperidine (400.0 mg, 0.952 mmol) in N,N-dimethylformamide, and the resulting mixture was stirred at 60° C. for 3 hours. The reaction was terminated by adding water (20 ml), followed by extraction with diethyl ether. The extract layer was washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent, whereby the title compound (426.7 mg, 0.952 mmol) was quantitatively obtained.

Workup

customThe reaction was terminated
additionby adding water (20 ml)
extractionfollowed by extraction with diethyl ether
washThe extract layer was washed with an aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
distillationdistilled under reduced pressure

Sources & evidence

ORD record: ord-ec5ac8c072cc4487a5aa1914551c65a0
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787560B2

Reaction notes

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