Acetic Acid → trans-N-(1-Cyclohexylethyl)-2-phenylcyclopropanamine

HRID 529329

Reaction equation

HRID 529329 reaction equation
[CH:1]1([C:7](=O)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[C:14]1([C@@H:20]2[CH2:22][C@H:21]2[NH2:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:1]1([CH:7]([NH:23][C@@H:21]2[CH2:22][C@H:20]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 13207Cyclohexyl methyl ketoneHCID 19493(1R,2S)-TranylcypromineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68385284trans-N-(1-Cyclohexylethyl)-2-phenylcyclopropanamineYield 24.95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-cyclohexylethanone (95 mg, 0.751 mmol) in 1,2-dichloroethane (DCE) (40 mL) and acetic acid (0.052 mL, 0.901 mmol) was added [(trans)-2-phenylcyclopropyl]amine (100 mg, 0.751 mmol). The reaction mixture was stirred for 2 hour at room temperature, then sodium triacetoxyborohydride (477 mg, 2.252 mmol) was added and the reaction mixture was stirred 3 hours at room temperature. The reaction mixture was quenched with saturated NH4Cl. Water (20 mL) followed by dichloromethane (40 mL) were added. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The solid was suspended in diethylether, sonicated and filtered. trans-N-(1-Cyclohexylethyl)-2-phenylcyclopropanamine (48 mg, 0.187 mmol, 24.95% yield) was isolated as white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.11-9.35 (m, 1H), 8.80-9.03 (m, 1H), 7.27-7.42 (m, 2H), 7.13-7.27 (m, 3H), 3.23 (br. s., 1H), 2.91 (d, J=2.78 Hz, 1H), 2.57 (ddd, J=3.54, 6.44, 9.98 Hz, 1H), 1.68-1.87 (m, 4H), 1.57-1.68 (m, 2H), 1.46-1.57 (m, 1H), 1.26-1.42 (m, 1H), 1.18-1.24 (m, 3H), 0.95-1.18 (m, 4H); LC-MS Rt=0.83 min; MS (ESI): 244.2 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred 3 hours at room temperature
  2. customThe reaction mixture was quenched with saturated NH4Cl
  3. additionwere added
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customsonicated
  10. filtrationfiltered

Sources & evidence

ORD record
ord-0617bb717f3a463b98c658422897c607
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Linked notes

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