Benzoyl chloride → N-isobutyl-N-[(1S)-1-phenylprop-2-en-1-yl]benzamide

HRID 1392107Notes

Reaction equation

HRID 1392107 reaction equation
[CH2:1]([NH:5][C@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:7]=[CH2:8])[CH:2]([CH3:4])[CH3:3].C(NC(C)C)(C)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:1]([N:5]([C@H:6]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH2:8])[C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7912DiisopropylamineHCID 58691167HCID 58691167, compound

Product 1

HCID 69213430N-isobutyl-N-[(1S)-1-phenylprop-2-en-1-yl]benzamideYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S)-N-isobutyl-1-phenylprop-2-en-1-amine (9a) (25 mg) and diisopropylamine (19 mg) in DCM (2.5 ml) at RT under N2 was added benzoyl chloride (21 mg). This mixture was stirred for 1 h. The reaction was evaporated and purified by flash chromatography (2% EtOAc/hexane) to afford the title compound (15 mg, 44%) as a pale oil. 1H NMR (300 MHz, CDCl3) δ 0.70 (d, 6H, J=6.6 Hz), 0.81 (bs, 3H), 1.75 (bs, 1H), 2.99-3.06 (m, 1H), 3.25-3.32 (m, 1H), 5.20-5.28 (m, 1H), 5.41 (d, 1H, J=9 Hz), 6.16 (bs, 1H), 7.25-7.46 (m, 5H). MS APCI, m/z=294 (M+1), LC/MS, 2.78 min. Chiral SFC was used to determine ee % by comparing this sample to a known sample of the racemic compound N-isobutyl-N-[(1-phenylprop-2-en-1-yl]benzamide 2.128 min (2.92%) and 2.639 min (97.07%) or 94% ee. Chiral SFC method: 5 μm Chiralpak AS-H column 4.6 mm×250 mm. Isocratic method 10% MeOH in carbon dioxide @ 2.20 ml/mn over 4 minutes.

Workup

  1. customThe reaction was evaporated
  2. custompurified by flash chromatography (2% EtOAc/hexane)

Sources & evidence

ORD record
ord-e6405e2797e54305a7482417258ec884
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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