Methylamine → 4-(Methylamino)cyclohexanecarbonitrile

HRID 539585Notes

Reaction equation

HRID 539585 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].[CH3:10][NH2:11].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.C(Cl)Cl>[CH3:10][NH:11][CH:6]1[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 122356394-Oxocyclohexane-1-carbonitrile

Product 1

HCID 574826414-(Methylamino)cyclohexanecarbonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of 4-cyanocyclohexanone (200 mg, 1.626 mmol) and CH3NH2 (2M in THF) (0.8 mL, 1.626 mmol) in THF:CH2Cl2 (1:1) (4.0 mL) at 0° C. was added NaBH(OAc)3 (689 mg, 3.252 mmol) and the resulting mixture was stirred at rt for 48 h. Subsequently, the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with water, brine, dried over Na2SO4 and concentrated to afford 200 mg (89%) of 4-(methylamino)cyclohexanecarbonitrile as a white solid. 1H NMR (400 MHz, DMSO-d6) 2.91 & 2.61 (two signals, 1H) 2.23-2.24 (m, 3H) 1.02-1.99 (m, 9H); ELSD/MS (Method 3) (m/z): [M+H]+ 139.06.

Workup

  1. customSubsequently, the solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-74c6f3aae30d4a62888d2ffecd1ef567
Source dataset
uspto-grants-2014_10
Patent number
US08871754B2

Reaction notes

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