Ethylamine → (2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamide

HRID 749457Notes

Reaction equation

HRID 749457 reaction equation
[CH2:1]([NH2:3])[CH3:2].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([CH2:15][CH:16]=[CH2:17])[C:12](Cl)=[O:13])=[CH:7][CH:6]=1>C(Cl)Cl>[CH2:1]([NH:3][C:12](=[O:13])[C@H:11]([C:8]1[CH:7]=[CH:6][C:5]([F:4])=[CH:10][CH:9]=1)[CH2:15][CH:16]=[CH2:17])[CH3:2]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 15536025(S)-2-(4-fluorophenyl)pent-4-enoyl chloride

Product 1

HCID 68978786(2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamideYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stream of ethylamine was introduced to ice-cooled CH2Cl2 (5 mL) until 350 mg gas had been consumed. A solution of (2S)-2-(4-fluorophenyl)pent-4-enoyl chloride (0.24 g in 5 mL of CH2Cl2, 1.1 mmol) was added dropwise. The mixture was stirred at room temperature for 1 h and then diluted with CH2Cl2 (10 mL). The solution was washed with aqueous solutions of KHSO4 (8 mL, 1M), NaOH (8 mL, 1M) and then brine. The organic solution was dried over Na2SO4 and then the solvent was evaporated. There was obtained 0.15 g (59%) of (2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamide. 1H NMR (500 MHz, CDCl3): 1.1 (t, 3H), 2.5 (m, 1H), 2.8-3.0 (m, 2H), 3.2-3.4 (m, 3H), 5.0-5.1 (m, 2H), 5.6-5.8 (m, 1H), 7.0 (t, 2H), 7.3 (m, 2H).

Workup

  1. customhad been consumed
  2. washThe solution was washed with aqueous solutions of KHSO4 (8 mL, 1M), NaOH (8 mL, 1M)
  3. dry with materialThe organic solution was dried over Na2SO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dbc78ff35b2941078b77e2bcd200f3c8
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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