Water → [2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine

HRID 749442Notes

Reaction equation

HRID 749442 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:19][CH:20]=[CH2:21])[C:15]([NH:17][CH3:18])=O)=[CH:10][CH:9]=1.O.[OH-].[Na+]>CCOCC>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH2:19][CH:20]=[CH2:21])[CH2:15][NH:17][CH3:18])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 689772612-(4-fluorophenyl)-N-methylpent-4-enamide

Product 1

HCID 18354439[2-(4-Fluorophenyl)pent-4-en-1-yl]methylamineYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminium hydride (0.11 g, 2.9 mmol) was slurried in ether (15 mL) under nitrogen with stirring. A solution of 2-(4-fluorophenyl)-N-methylpent-4-enamide (0.20 g in 5 mL of ether, 0.97 mmol) was added carefully and the mixture was then stirred at room temperature overnight. Water (0.11 mL) was added dropwise followed by a solution of NaOH (0.11 mL of a 15% aqueous solution) and then water (0.33 mL) again. The mixture was stirred for 10 min and then filtered. The filter cake was washed with ether and the combined solutions were washed several times with water. The organic solution was dried over MgSO4 and the solvent was removed by evaporation. There was obtained 0.16 g (86%) of [2-(4-fluorophenyl)pent-4-en-1-yl]methylamine as an oil. 1H NMR (400 MHz, CDCl3): 2.4-2.6 (m, 5H), 2.7-2.9 (m, 3H), 4.9-5.0 (m, 2H), 5.6-5.8 (m, 1H), 7.0 (m, 2H), 7.1 (m, 2H); LCMS: m/z 194 (M+1)+.

Workup

  1. stirringthe mixture was then stirred at room temperature overnight
  2. stirringThe mixture was stirred for 10 min
  3. filtrationfiltered
  4. washThe filter cake was washed with ether
  5. washthe combined solutions were washed several times with water
  6. dry with materialThe organic solution was dried over MgSO4
  7. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-f47292380cff48629ebb3e2a4b5ce84e
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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