Ethyl Bromide → (1-Ethylpiperidin-3-yl)methanol

HRID 603185Notes

Reaction equation

HRID 603185 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[CH3:16]>CN(C)C=O>[CH2:15]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1)[CH3:16]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 20439432(1-Ethylpiperidin-3-yl)methanolYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of piperidin-3-ylmethanol (3.88 g) in dimethylformamide (50 mL) was added potassium carbonate (9.3 g) and ethyl bromide (2.52 mL). The reaction was stirred overnight at room temperature. The mixture was filtered and the filtrate evaporated. The residue was filtered through a short pad of silica eluting with 10% 7M NH3/MeOH in dichloromethane. The filtrate was evaporated to give the title compound as an orange oil (4.8 g, 99%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. filtrationThe residue was filtered through a short pad of silica eluting with 10% 7M NH3/MeOH in dichloromethane
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a6a42df75e37456caa40517d23372d15
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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