Propanal → N1,N1-dimethyl-N4-propyl-1,4-Butanediamine

HRID 2261902Notes

Reaction equation

HRID 2261902 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH:9](=O)[CH2:10][CH3:11].[BH4-].[Na+]>CO>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 527PropanalHCID 770634-DimethylaminobutylamineHCID 4311764Sodium borohydride

Product 1

HCID 21520995N1,N1-dimethyl-N4-propyl-1,4-Butanediamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N1,N1-dimethylbutane-1,4-diamine (0.64 g, 5.5 mmol) and propionaldehyde (0.38 mL, 5.2 mmol) in 20 mL methanol was stirred at rt overnight. Sodium borohydride (0.31 g, 8.3 mmol) was added and the reaction mixture was stirred for 20 min. The reaction was quenched with 1N NaOH, extracted with ether and washed with brine. Drying, solvent evaporation and flash chromatography (0-12% [10% NH4OH/MeOH]/CH2Cl2) gave N1,N1-dimethyl-N4-propylbutane-1,4-diamine. 1H NMR (CDCl3) δ 2.61 (t, J=6.7 Hz, 2H), 2.57 (t, J=7.2 Hz, 2H), 2.26 (t, J=7.0 Hz, 2H), 2.21 (s, 6H), 1.49 (m, 6H), 0.91 (t, J=7.4 Hz, 3H).

Workup

  1. customThe reaction was quenched with 1N NaOH
  2. extractionextracted with ether
  3. washwashed with brine
  4. customDrying
  5. customsolvent evaporation and flash chromatography (0-12% [10% NH4OH/MeOH]/CH2Cl2)

Sources & evidence

ORD record
ord-451c7ad08b7b4877b3e4d9a1d1014cae
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

Loading…