3-Methoxy-1-azetidineacetonitrile → HCID 55285918, compound

HRID 1669199Notes

Reaction equation

HRID 1669199 reaction equation
[CH3:1][O:2][CH:3]1[CH2:6][N:5]([CH2:7][C:8]#[N:9])[CH2:4]1>[Ni].CCO>[CH3:1][O:2][CH:3]1[CH2:6][N:5]([CH2:7][CH2:8][NH2:9])[CH2:4]1

Participants

4

Reactant 1

HCID 574476933-Methoxy-1-azetidineacetonitrile

Product 1

HCID 55285918HCID 55285918, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of nitrile 276 (1.76 g, 14.0 mmol), cNH3 (7 mL) and Raney Nickel (50% slurry in water, 4.6 g) in EtOH (100 mL) was stirred under H2 (60 psi) for 5 h. The mixture was filtered through Celite, washed with EtOH (50 mL) and the solvent was evaporated to give crude diamine 277 (950 mg, 52%) as a yellow oil, which was used without further purification: 1H NMR δ 4.03 (p, J=5.8 Hz, 1H, CHO), 3.58-3.63 (m, 2H, CH2N), 3.25 (s, 3H, OCH3), 2.88-2.93 (m, 2H, CH2N), 2.67 (t, J=6.0 Hz, 2H, CH2N), 2.52 (t, J=6.0 Hz, 2H, CH2N), NH2 not observed; MS (APCI) m/z 131 (MH+, 100%); HRMS (FAB+) calcd for C6H15N2O (MH+) m/z 131.1184, found 131.1183.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with EtOH (50 mL)
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3ca8f2d2c9694c05a4f73a61b08c4365
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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