p-Fluorophenethylamine → (2E)-N-[2-(4-Fluorophenyl)ethyl]-2-butenamide

HRID 896535Notes

Reaction equation

HRID 896535 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:22])/[CH:19]=[CH:20]/[CH3:21]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:18](=[O:22])/[CH:19]=[CH:20]/[CH3:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4653p-FluorophenethylamineHCID 8471TriethylamineHCID 643131trans-Crotonyl chloride

Product 1

HCID 86591719(2E)-N-[2-(4-Fluorophenyl)ethyl]-2-butenamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-fluorophenyl)ethylamine (13.25 mL, 100 mmol) and triethylamine (14.6 mL, 105 mmol) in dichloromethane (375 mL) was stirred on an ice bath. A solution of crotonyl chloride (10.65 mL, 100 mmol) in dichloromethane (25 mL) was added dropwise over 15 minutes. The cooling bath was removed and the solution was stirred at room temperature for 2 hours. It was then washed twice with 1.0 N aqueous hydrochloric acid, then twice with saturated aqueous sodium hydrogen carbonate. The organic phase was dried over sodium sulfate and concentrated under vacuum to provide a yellowish solid (20.78 g, quantitative). Recrystallization from toluene provided white needles (15.5 g, 75%), mp 121-123° C. 1H NMR (300 MHz, CDCl3) δ7.16 (m, 2H), 7.01 (t, J=9 Hz, 2H), 6.85 (dq, J=15, 7 Hz, 1H), 5.74 (dd, J=15, 1 Hz, 1H), 5.49 (bs, 1H), 3.56 (m, 2H), 2.83 (t, J=7 Hz, 2H), 1.85 (dd, J=7, 2 Hz, 3H). Mass spec (ES+) m/z 249.0 (M+H+acetonitrile+, 100%).

Workup

  1. customThe cooling bath was removed
  2. washIt was then washed twice with 1.0 N aqueous hydrochloric acid
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto provide a yellowish solid (20.78 g, quantitative)
  6. customRecrystallization from toluene provided white needles (15.5 g, 75%), mp 121-123° C

Sources & evidence

ORD record
ord-8112a0d4e4614b4db299240f7a853220
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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