Benzaldehyde → 3-benzyl-N-{4-[trans-2-(benzylamino)cyclopropyl]phenyl}benzamide

HRID 922509Notes

Reaction equation

HRID 922509 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:27])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)=[CH:8][CH:7]=1.[CH:28](=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])O.[Na+].[BH4-].[Na+]>CO.O>[CH2:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:13]([NH:12][C:9]1[CH:8]=[CH:7][C:6]([C@@H:4]2[CH2:5][C@H:3]2[NH:2][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:11][CH:10]=1)=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86729847N-[4-(trans-2-aminocyclopropyl)phenyl]-3-benzylbenzamide hydrochloride

Product 1

HCID 902141983-benzyl-N-{4-[trans-2-(benzylamino)cyclopropyl]phenyl}benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-[4-(trans-2-aminocyclopropyl)phenyl]-3-benzylbenzamide hydrochloride (69.6 mg) in methanol (1.5 mL) were added benzaldehyde (19 μL) and sodium hydrogen carbonate (23.2 mg). The mixture was stirred at 70° C. for 1 hr, and ice-cooled to 0° C. and sodium borohydride (10.4 mg) was added. The mixture was stirred for 1 hr and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and crystallized (hexane/ethyl acetate) to give the title compound (29.7 mg).

Workup

  1. temperatureice-cooled to 0° C.
  2. stirringThe mixture was stirred for 1 hr
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  8. customcrystallized (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9b4977e3fbe34f61ace9b993a96da5b3
Source dataset
uspto-grants-2016_03
Patent number
US09278931B2

Reaction notes

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