4-(Trifluoromethyl)benzaldehyde → HCID 46869801, compound

HRID 882337Notes

Reaction equation

HRID 882337 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]([F:23])([F:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH:11][CH2:18][C:17]2[CH:16]=[CH:15][C:14]([C:13]([F:12])([F:22])[F:23])=[CH:21][CH:20]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 2723716Tranylcypromine hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 46869801HCID 46869801, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (trans)-2-phenylcyclopropanamine hydrochloride (0.23 g, 1.36 mmol) and 4-(trifluoromethyl)benzaldehyde (0.20 mL, 1.49 mmol) in CH2Cl2 (8 mL) and water (0.5 mL) was vigorously stirred at room temperature for 10 min. Then, NaBH(OAc)3 (0.37 g, 1.76 mmol) was slowly added and stirring continued for 30 min. The reaction mixture was washed with an aqueous saturated solution of NaHCO3 (8 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 (1% MeOH/CH2Cl2) affording 0.15 g of N-[(trans)-2-phenylcyclopropyl]-N-[4-(trifluoromethyl)benzyl]amine [Rf=0.6 (5% MeOH/CH2Cl2), colorless oil, 38% yield].

Workup

  1. stirringstirring
  2. waitcontinued for 30 min
  3. washThe reaction mixture was washed with an aqueous saturated solution of NaHCO3 (8 mL)
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customafter removal of the solvent
  7. customthe residual oil was purified by column chromatography on silica gel (1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-66d7fbcb5c384fe09bc71cb43594ef34
Source dataset
uspto-grants-2015_03
Patent number
US08993808B2

Reaction notes

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