Tetrahydro-1,4-oxazepine-4(5H)-acetonitrile → 878155-50-1

HRID 1669208Notes

Reaction equation

HRID 1669208 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]#[N:10])[CH2:3][CH2:2]1>CCO.[Ni]>[O:1]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][CH2:9][NH2:10])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 62059577Tetrahydro-1,4-oxazepine-4(5H)-acetonitrile

Product 1

HCID 57640201878155-50-1Yield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of nitrile 293 (3.2 g, 22.8 mmol) and Raney-Nickel (50% w/w in water, ca. 12 g) in EtOH (100 mL) and cNH3 (10 mL) was stirred under H2 (60 psi) for 16 h. The mixture was filtered through Celite, washed with EtOH (3×10 mL) and the solvent evaporated to give crude diamine 294 (2.98 g, 91%) as a pale yellow oil, which was used without further purification: 1H NMR [(CD3)2SO] δ 3.64-3.67 (m, 2H, H-3), 3.57-3.59 (m, 2H, H-5), 2.49-2.62 (m, 8H, H-2, H-7, 2×CH2), 1.71-1.80 (m, 2H, H-6), NH2 not observed; HRMS (FAB+) calcd for C7H17N2O (MH+) m/z 145.13409, found 145.13439.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with EtOH (3×10 mL)
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-b87f981258b84f39807e048cb7f004b2
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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