Water → 1-Ethyl-3-(3-fluorobenzyl)piperidine

HRID 928076Notes

Reaction equation

HRID 928076 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=O)[CH3:19])[CH2:13]1.O>C1COCC1>[CH2:18]([N:14]1[CH2:15][CH2:16][CH2:17][CH:12]([CH2:11][C:10]2[CH:21]=[CH:22][CH:23]=[C:8]([F:7])[CH:9]=2)[CH2:13]1)[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 710069491-[3-(3-Fluorobenzyl)piperidin-1-yl]ethanone2×

Product 1

HCID 709845911-Ethyl-3-(3-fluorobenzyl)piperidineYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminium hydride (2M in THF, 2.8 mL) was added dropwise to a solution of 1-[3-(3-fluorobenzyl)piperidin-1-yl]ethanone (Intermediate 224, 0.66 g) in anhydrous THF (20 mL) at 0° C. under argon. The mixture was stirred for 30 minutes then allowed to warm to room temperature and stirred for 2 hours. The mixture was recooled to 0° C. and water was added. The mixture was extracted with ether, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 1-ethyl-3-(3-fluorobenzyl)piperidine (0.535 g).

Workup

  1. stirringstirred for 2 hours
  2. customwas recooled to 0° C.
  3. extractionThe mixture was extracted with ether
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-45bc1193ba7748f993d5650b3de38942
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

Loading…