4-Fluorobenzaldehyde → N-(4-fluorobenzyl)-N-[(trans)-2-phenylcyclopropyl]amine
Reaction equation
Cl.[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:11][C@@H:9]2[CH2:10][C@H:8]2[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:15][CH:14]=1Participants
6
Procedure
A mixture of (trans)-2-phenylcyclopropanamine hydrochloride (0.25 g, 1.50 mmol) and 4-fluorobenzaldehyde (0.18 mL, 1.65 mmol) in CH2Cl2 (8 mL) and water (0.5 mL) was vigorously stirred at room temperature for 10 min. Then, NaBH(OAc)3 (0.41 g, 1.95 mmol) was slowly added and stirring continued for 1.5 h. The reaction mixture was washed with an aqueous saturated solution of NaHCO3 (10 mL), the organic layer was dried over anhydrous Na2SO4, filtered and, after removal of the solvent, the residual oil was purified by column chromatography on silica gel (3% MeOH/CH2Cl2) affording 0.18 g of N-(4-fluorobenzyl)-N-[(trans)-2-phenylcyclopropyl]amine [Rf=0.5 (5% MeOH/CH2Cl2), colorless oil, 49% yield].
Workup
- stirringstirring
- waitcontinued for 1.5 h
- washThe reaction mixture was washed with an aqueous saturated solution of NaHCO3 (10 mL)
- dry with materialthe organic layer was dried over anhydrous Na2SO4
- filtrationfiltered
- customafter removal of the solvent
- customthe residual oil was purified by column chromatography on silica gel (3% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-ef3aa42e11e041048a0777e3ae607b4e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993808B2
Reaction notes
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