Benzoyl chloride → N-benzyl-N-[(1S)-1-phenylprop-2-en-1-yl]cyclopentanamine

HRID 1392101Notes

Reaction equation

HRID 1392101 reaction equation
[C:1]1([C@@H:7]([NH:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=[CH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(NC(C)C)(C)C.[C:23](Cl)(=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([N:10]([C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:8]=[CH2:9])[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7912DiisopropylamineHCID 58691178HCID 58691178, compound

Product 1

HCID 69211090N-benzyl-N-[(1S)-1-phenylprop-2-en-1-yl]cyclopentanamineYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1S)-1-phenylprop-2-en-1-yl]cyclopentanamine (24 mg) and diisopropylamine (18 mg) in DCM (2.5 ml) at RT under N2 was added benzoyl chloride (20 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 1.22-2.27 (m, 8H), 3.57 (bs, 1H), 5.28-5.60 (m, 3H), 6.23 (bs, 1H), 7.00-7.71 (m, 10H). MS APCI, m/z=306 (M+1), LC/MS, 2.83 min. Chiral HPLC was used to determine ee % by comparing this sample to a known sample of the racemic compound N-benzyl-N-(1-phenylprop-2-en-1-yl)cyclopentanamine. 14.99 min (97.89%) and 17.52 min (2.11%) or 96% ee. Chiral HPLC method: Chiral Technologies 10 μm Chiralpak AD column 4.6 mm×250 mm. Solvents: A=IPA, B=Hexane. Isocratic Method 7% A/B over 30 minutes at 0.6 ml/mn.

Workup

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

Sources & evidence

ORD record
ord-e7e66ef050414755a7cba03b0208e6f3
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

Loading…