Sodium Cyanide → HCID 57904789, compound

HRID 1093073Notes

Reaction equation

HRID 1093073 reaction equation
[NH4+:1].[OH-].[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1.[NH4+:12].[Cl-].[C-:14]#N.[Na+]>CO>[NH2:1][C:8]1([C:14]#[N:12])[CH2:9][CH2:10][CH:5]([CH2:4][OH:3])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 128928674-(Hydroxymethyl)cyclohexan-1-one

Product 1

HCID 57904789HCID 57904789, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of NH4OH (125 mL) and methanol (50 mL) was added 4-(hydroxymethyl)cyclohexanone (10 g, 78 mmol), NH4Cl (8.35 g, 156 mmol) and NaCN (7.65 g, 156 mmol). After 16 h at room temperature, the reaction mixture was extracted with CH2Cl2 (250 mL×2), and 4:1 chloroform:2-propanol, and the combined organic fractions washed with water (500 mL), dried (Na2SO4), filtered and concentrated to afforded the title compound as a colorless liquid (8 g, 67% yield). 1H NMR (500 MHz, CDCl3) δ: 3.51 (d, 2H, J=4.58 Hz), 2.07-2.09 (m, 2H), 1.86-1.91 (m, 4H), 1.68 (s, 2H), 1.47-1.53 (m, 3H), 1.41 9 brs, 1H), 1.30-1.36 9 m, 2H). LCMS (M+H)=155.18.

Workup

  1. extractionthe reaction mixture was extracted with CH2Cl2 (250 mL×2), and 4:1 chloroform
  2. wash2-propanol, and the combined organic fractions washed with water (500 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-57faaf0658c64049b1b0f7abc65eb60a
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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