Sodium Cyanide → HCID 67958695, compound

HRID 75724Notes

Reaction equation

HRID 75724 reaction equation
[F:1][C:2]1([CH2:9][OH:10])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[OH-].[NH4+:12].[NH4+:13].[Cl-].[C-:15]#N.[Na+]>CO>[NH2:12][C:5]1([C:15]#[N:13])[CH2:6][CH2:7][C:2]([F:1])([CH2:9][OH:10])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium Chloride2×HCID 67958901HCID 67958901, compound

Product 1

HCID 67958695HCID 67958695, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask was charged with 4-fluoro-4-(hydroxymethyl)cyclohexanone, derived from Intermediate 31, (12.1 g, 83 mmol), methanol (200 mL), aqueous ammonium hydroxide (32.2 mL, 828 mmol) and then NH4Cl (8.86 g, 166 mmol). After the ammonium chloride had dissolved, NaCN (8.11 g, 166 mmol) was added. The reaction was stirred under nitrogen overnight. The mixture was then concentrated. Brine (100 mL) was added to the resulting residue. The slurry was extracted with chloroform/isopropanol (200 mL, 10%, 7 times) and the combined organic fractions dried (MgSO4) and evaporated giving the title compound (12.2 g, 70.8 mmol, 86% yield)] as a creamy white solid.

Workup

  1. concentrationThe mixture was then concentrated
  2. additionBrine (100 mL) was added to the resulting residue
  3. extractionThe slurry was extracted with chloroform/isopropanol (200 mL, 10%, 7 times)
  4. dry with materialthe combined organic fractions dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-40cf5d4fc97644af89a64ae189ef280d
Source dataset
uspto-grants-2014_09
Patent number
US08835411B2

Reaction notes

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