Methanol → 1555-57-3

HRID 1419503Notes

Reaction equation

HRID 1419503 reaction equation
[NH:1]([CH2:6][CH2:7][C:8]#[N:9])[CH2:2][CH2:3][C:4]#[N:5].CO.C([BH3-])#N.[Na+].[C:16](#N)[CH3:17]>>[C:4]([CH2:3][CH2:2][N:1]([CH2:6][CH2:7][C:8]#[N:9])[CH2:16][CH3:17])#[N:5]

Participants

5

Reactant 4

HCID 887MethanolHCID 6342AcetonitrileHCID 81493,3'-IminodipropionitrileHCID 5003444Sodium cyanoborohydride

Product 1

HCID 150760341555-57-3Yield 52%

Procedure

To a stirred mixture of 3,3'-iminodipropionitrile (14.4 g, 0.117 mol), acetaldelyde (25.7 g, 0.584 mol), methanol 50 mL), and acetonitrile (400 mL) was added sodium cyanoborohydride (9.6 g, 0.152 mol). The mixture was allowed to stir at room temperature overnight. The solvent was evaporated. The resulting residue was partitioned between dichloromethane and H2O. The dichloromethane layer was washed with water, dried, and evaporated to give a yellow oil, which was distilled by a Kugelrohr apparatus to give the title compound (9.2 g, 52%). 1H NMR (CDCl3, 200 MHz) 2.86 (t, J=7.0 Hz, 4H), 2.64 (q, J=7.0 Hz, 4H), 2.48 (t, J=7.0 Hz, 4H), 1.08 (t, J=7.0 Hz, 3H).

Workup

  1. customThe solvent was evaporated
  2. customThe resulting residue was partitioned between dichloromethane and H2O
  3. washThe dichloromethane layer was washed with water
  4. customdried
  5. customevaporated
  6. customto give a yellow oil, which
  7. distillationwas distilled by a Kugelrohr apparatus

Sources & evidence

ORD record
ord-2d99c07923ef447496f953130f4152fb
Source dataset
uspto-grants-1999_03
Patent number
US05886185

Reaction notes

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