4-Cyanobenzaldehyde → HCID 46869800, compound

HRID 882335Notes

Reaction equation

HRID 882335 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.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)#[N:13].[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:20]=[CH:21][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 2723716Tranylcypromine hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 46869800HCID 46869800, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (trans)-2-phenylcyclopropanamine hydrochloride (0.25 g, 1.50 mmol) and 4-cyanobenzaldehyde (0.22 g, 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 (1% MeOH/CH2Cl2) affording 0.07 g of 4-({[(trans)-2-phenylcyclopropyl]amino}methyl)benzonitrile [Rf=0.6 (5% MeOH/CH2Cl2), colorless oil, 19% yield].

Workup

  1. stirringstirring
  2. waitcontinued for 1.5 h
  3. washThe reaction mixture was washed with an aqueous saturated solution of NaHCO3 (10 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-e811af39cc6b43f8a860b3b77b10df35
Source dataset
uspto-grants-2015_03
Patent number
US08993808B2

Reaction notes

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