Hydrogen Bromide → 3-(Bromomethyl)-1-ethylpiperidine

HRID 1044849Notes

Reaction equation

HRID 1044849 reaction equation
[BrH:1].[CH2:2]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([CH2:10]O)[CH2:5]1)[CH3:3].O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Br:1][CH2:10][CH:6]1[CH2:7][CH2:8][CH2:9][N:4]([CH2:2][CH3:3])[CH2:5]1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 11430Potassium CarbonateHCID 20439432(1-Ethylpiperidin-3-yl)methanol

Product 1

HCID 215104883-(Bromomethyl)-1-ethylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

48% Aqueous hydrogen bromide (16 ml) was added to N-ethyl-3-piperidinemethanol (1.53 g) and the stirring mixture refluxed for 6 hours. After cooling, the solvent was stripped, the residue treated with water and made basic by addition of 1M aq. potassium carbonate. The mixture was shaken with dichloromethane, filtered to remove unwanted solid, and the filtrate separated. The aqueous layer was further extracted with dichloromethane and the combined extracts washed with dilute brine, dried by passing through a phase separation cartridge and stripped to give the title compound as a pale oil (1.4 g).

Workup

  1. temperaturethe stirring mixture refluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. customto remove unwanted solid
  5. customthe filtrate separated
  6. extractionThe aqueous layer was further extracted with dichloromethane
  7. washthe combined extracts washed with dilute brine
  8. customdried
  9. customby passing through a phase separation cartridge

Sources & evidence

ORD record
ord-2f5bbce018864bd39eee0350042b5b71
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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