Ethyl Bromide → 1-Ethyl-4-(3-fluorobenzyl)piperidine

HRID 928046Notes

Reaction equation

HRID 928046 reaction equation
Br[CH2:2][CH3:3].[F:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][CH:17]=1)[CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:2]([N:12]1[CH2:13][CH2:14][CH:9]([CH2:8][C:7]2[CH:15]=[CH:16][CH:17]=[C:5]([F:4])[CH:6]=2)[CH2:10][CH2:11]1)[CH3:3]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 107281414-[(3-Fluorophenyl)methyl]piperidine2×

Product 1

HCID 709836871-Ethyl-4-(3-fluorobenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromoethane (0.1 mL) was added to a mixture of 4-(3-fluorobenzyl)piperidine (Intermediate 180, 0.259 g) and potassium carbonate (0.204 g) in acetonitrile (10 mL). The mixture was stirred for 20 hours then filtered. The filtrate acidified by addition of few drops of 2M HCl and the solution was passed through a SCX-2 column (10 g). The product was eluted with 2M ammonia in methanol and the residue after evaporation was triturated with diethyl ether. The solid was filtered off and the filtrated was concentrated in vacuo to give 1-ethyl-4-(3-fluorobenzyl)piperidine (0.210 g)

Workup

  1. filtrationthen filtered
  2. additionThe filtrate acidified by addition of few drops of 2M HCl
  3. washThe product was eluted with 2M ammonia in methanol
  4. customthe residue after evaporation
  5. customwas triturated with diethyl ether
  6. filtrationThe solid was filtered off
  7. concentrationthe filtrated was concentrated in vacuo

Sources & evidence

ORD record
ord-9831bd9934d44785b9a1154d29da9e4c
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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