Sodium Cyanide → HCID 67259282, compound

HRID 2423378Notes

Reaction equation

HRID 2423378 reaction equation
[CH2:1]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][C:15]2=O)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C-:22]#[N:23].[Na+].[Cl-].[NH4+:26]>[OH-].[NH4+]>[NH2:26][C:15]1([C:22]#[N:23])[CH2:16][CH2:17][CH2:18][CH:14]1[CH2:13][C:12]1[CH:20]=[CH:21][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 67259190HCID 67259190, compound

Product 1

HCID 67259282HCID 67259282, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

2-(4-Octylbenzyl)cyclopentanone (5) 3.20 g (11.8 mmol), sodium cyanide 1.15 g (23.5 mmol) and ammonium chloride 1.25 g (23.5 mmol) were added to 20 mL of ammonium hydroxide. The mixture was stirred vigorously for 12 hours at room temperature, then poured into a separating funnel and extracted twice with 10 mL of methylene chloride. The organic layers were combined, dried and then concentrated to give a crude yellow oil (3.30 g, ˜100%). The crude product is used for next step without further purification. (See: J. Med. Chem., 1986, 29, 1988-1995).

Workup

  1. additionpoured into a separating funnel
  2. extractionextracted twice with 10 mL of methylene chloride
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0bfd71ae0c2444aa81ba7ea5f17be8f6
Source dataset
uspto-grants-2011_06
Patent number
US07960588B2

Reaction notes

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