Benzaldehyde → HCID 8032053, compound

HRID 1292667Notes

Reaction equation

HRID 1292667 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([BH3-])#N.[Na+].[BH4-].[Na+]>CC#N.C1COCC1.C(O)(=O)C>[CH2:17]([NH:10][CH2:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 796983,3-DiphenylpropylamineHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 8032053HCID 8032053, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,3-diphenylpropylamine (1.01 g, 4.79 mmol), acetic acid (28 ml, 049 mmol), and benzaldehyde (490 μl, 4.80 mmol) in CH3CN (2 ml) was added sodium cyanoborohydride (4.80 ml of a 1M solution in THF, 4.8 mmol) at 0° C. The reaction was allowed to warm to room temperature and stirred for 18 hrs. The solvent was evaporated in vacuo, quenched with sat. aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo. The residue was dissolved in MeOH (100 ml) and sodium borohydride (182 mg, 5.55 mmol) added and the reaction was stirred for 30 min. The solvent was evaporated and the residue treated with sat. aq. NaHCO3 and extracted with EtOAc. The organic layer was separated, washed with saturated brine, dried (Na2SO4) and the solvent evaporated in vacuo to afford the title compound as an oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customquenched with sat. aq. NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. dissolutionThe residue was dissolved in MeOH (100 ml)
  8. stirringthe reaction was stirred for 30 min
  9. customThe solvent was evaporated
  10. additionthe residue treated with sat. aq. NaHCO3
  11. extractionextracted with EtOAc
  12. customThe organic layer was separated
  13. washwashed with saturated brine
  14. dry with materialdried (Na2SO4)
  15. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c35860bb8dbb4f55b144e2df723cd484
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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