Formaldehyde → HCID 21834627, compound

HRID 1292668Notes

Reaction equation

HRID 1292668 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:26]([BH3-])#N.[Na+]>CC#N.O>[CH2:1]([N:8]([CH2:9][CH2:10][CH:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 8032053HCID 8032053, compound

Product 1

HCID 21834627HCID 21834627, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of N-benzyl-3,3-diphenylpropylamine (1.29 g, 4.30 mmol) and 30% aq. formaldehyde (1.50 ml, 20 mmol) in CH3CN:H2O (2:1, v/v, 40 ml) was added sodium cyanoborohydride (563 mg, 8.96 mmol) at 0° C. The reaction was allowed to warm to room temperature and stirred for 90 min. The organic solvent was evaporated, and the residue diluted with water and extracted with CH2Cl2. The organic extracts were washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo to afford the title compound as an oil.

Workup

  1. customThe organic solvent was evaporated
  2. additionthe residue diluted with water
  3. extractionextracted with CH2Cl2
  4. washThe organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-a36353313b1a478bbde77c19b719fd2c
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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