Propanal → HCID 10729576, compound

HRID 2190328Notes

Reaction equation

HRID 2190328 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)[CH2:18][CH3:19].[BH4-].[Na+]>CO>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][NH:10][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 527PropanalHCID 796983,3-DiphenylpropylamineHCID 4311764Sodium borohydride

Product 1

HCID 10729576HCID 10729576, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,3-diphenylpropan-1-amine 1 (4.22 g, 20.0 mmol) in MeOH (100 mL) at room temperature was added propionaldehyde (1.16 g, 20.0 mmol) (1.45 mL). The reaction mixture was stirred at room temperature for 3 h and sodium borohydride (1.20 g, 31.7 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, quenched with 5 M NaOH, partially concentrated, and diluted with EtOAc. The aqueous phase was extracted with EtOAc (2×) and combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 2% to 8% MeOH (2 M NH3) in DCM) gave 3,3-diphenyl-N-propylpropan-1-amine 7 as a pale yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 h
  2. customquenched with 5 M NaOH
  3. concentrationpartially concentrated
  4. additiondiluted with EtOAc
  5. extractionThe aqueous phase was extracted with EtOAc (2×)
  6. washwere washed with brine (1×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash column chromatography on silica gel (eluted with 2% to 8% MeOH (2 M NH3) in DCM)

Sources & evidence

ORD record
ord-97896ae16e7e4f65a5624f4e1dfe8a28
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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