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

HRID 1006063
Notes
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Reaction equation

HRID 1006063 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 226753214-(2-Bromo-5-hydroxybenzyl)-1-[(2-chlorophenyl)acetyl]piperidine

Product 1

HCID 226752854-(2-Bromo-5-ethoxybenzyl)-1-[(2-chlorophenyl)acetyl]piperidineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customThe reaction was terminated
  2. additionby adding water (20 ml)
  3. extractionfollowed by extraction with diethyl ether
  4. washThe extract layer was washed with an aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes