Sodium Hydroxide → 2-Bromo-1-(3,3-dimethylpiperidin-1-yl)ethanone

HRID 1950314Notes

Reaction equation

HRID 1950314 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[OH-].[Na+].[Br:11][CH2:12][C:13](Cl)=[O:14]>ClCCl>[Br:11][CH2:12][C:13]([N:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH3:8])([CH3:1])[CH2:3]1)=[O:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 709423,3-DimethylpiperidineHCID 89602Bromoacetyl chloride

Product 1

HCID 233637862-Bromo-1-(3,3-dimethylpiperidin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,3-dimethylpiperidine (250 mg) in dichloromethane (3 ml) was added an aqueous solution of 5N sodium hydroxide (1.1 ml), bromoacetyl chloride (0.2 ml) was added dropwise thereto on an ice bath, and the solution was stirred for 1 hour at room temperature. The solution was extracted with diethyl ether, then sequentially washed with an aqueous solution of 10% citric acid and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo to provide the title compound (420 mg).

Workup

  1. additionwas added dropwise
  2. extractionThe solution was extracted with diethyl ether
  3. washsequentially washed with an aqueous solution of 10% citric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6ea16c7608974c679828d116f76fae96
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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