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

HRID 2371143Notes

Reaction equation

HRID 2371143 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-7d8bd4f0a72243e8a6640e254f7c8262
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

Loading…