2-Pyridinecarboxaldehyde → HCID 46869802, compound

HRID 882339Notes

Reaction equation

HRID 882339 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.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=O.[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:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 2723716Tranylcypromine hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 46869802HCID 46869802, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (trans)-2-phenylcyclopropanamine hydrochloride (0.25 g, 1.50 mmol) and pyridine-2-carbaldehyde (0.17 mL, 1.80 mmol) in CH2Cl2 (12 mL) and water (0.5 mL) was vigorously stirred at room temperature for 10 min. Then, NaBH(OAc)3 (0.48 g, 2.25 mmol) was slowly added and stirring continued for 2 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 [4% MeOH+1% NH3 (aq)/CH2Cl2] followed by preparative layer chromatography (5% MeOH/CH2Cl2) affording 0.08 g of N-[(trans)-2-phenylcyclopropyl]-N-(pyridin-2-ylmethyl)amine [Rf=0.3 (5% MeOH/CH2Cl2), colorless oil, 24% yield]. 1H-NMR (CDCl3, 250 MHz, δ): 8.60-8.54 (m, 1H, ArH); 7.62 (td, J=7.8, 1.6 Hz, 1H, ArH); 7.28-7.09 (m, 5H, ArH); 7.03-6.97 (m, 2H, ArH); 4.01 (s, 2H, CH2); 2.44-2.37 (m, 1H, CH); 2.09 (br s, 1H, NH); 2.01-1.92 (m, 1H, CH); 1.19-1.10 (m, 1H, CH2); 1.02-0.94 (m, 1H, CH2).

Workup

  1. stirringstirring
  2. waitcontinued for 2 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 [4% MeOH+1% NH3 (aq)/CH2Cl2]

Sources & evidence

ORD record
ord-584fa9156cb44ed6ae3339f5a9f6c889
Source dataset
uspto-grants-2015_03
Patent number
US08993808B2

Reaction notes

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