3,5-Dichlorobenzoyl chloride → 3,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide

HRID 749454Notes

Reaction equation

HRID 749454 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:12][CH:13]=[CH2:14])[CH2:9][NH:10][CH3:11])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([Cl:34])[CH:33]=1)[C:28](Cl)=[O:29]>C(Cl)Cl>[Cl:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([Cl:34])[CH:33]=1)[C:28]([N:10]([CH2:9][C@H:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH2:12][CH:13]=[CH2:14])[CH3:11])=[O:29]

Participants

5

Reactant 3

HCID 761913,5-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 15536023[(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine

Product 1

HCID 689786383,5-Dichloro-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylbenzamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine (see Bioorg. Med. Chem. Lett; 2001; 265-270; 150 mg, 0.78 mmol) was dissolved in CH2Cl2 (5 mL) and to the resultant solution were added DIPEA (221 mg, 1.71 mmol) and 3,5-dichlorobenzoyl chloride (178 mg, 0.85 mmol) in the given order. The mixture was stirred for 4 h at room temperature, diluted with CH2Cl2 (20 mL), and then washed with water (10 mL), aqueous KHSO4 (1M, 10 mL) and brine (10 mL). The organic solution was dried over Na2SO4. The solvent was removed by evaporation and there was obtained 214 mg (75%) of 3,5-dichloro-N-[(2S)-2-(4fluorophenyl)pent-4-en-1-yl]-N-methylbenzamide as an oil. 1H NMR (500 MHz, CDCl3): 2.2-2.4 (cm, 2H), 2.6 (s, 2H), 2.9-3.9 (cm, 4H), 4.9-5.1 (m, 2H), 5.5-5.8 (m, 1H), 6.7 (s, 1H), 6.9-7.4 (cm, 6H); LCMS: m/z 367 (M+1)+.

Workup

  1. washwashed with water (10 mL), aqueous KHSO4 (1M, 10 mL) and brine (10 mL)
  2. dry with materialThe organic solution was dried over Na2SO4
  3. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-4a3a4b795e9a40e680c62894723dc47d
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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