Potassium Cyanide → 1-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)cycloheptane-carbonitrile

HRID 991458Notes

Reaction equation

HRID 991458 reaction equation
Cl.[O:2]=[C:3]1[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5][NH:4]1.[C:19]1(=O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[C-:27]#[N:28].[K+]>O>[O:2]=[C:3]1[C:7]2([CH2:8][CH2:9][N:10]([C:19]3([C:27]#[N:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:11][CH2:12]2)[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5][NH:4]1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 10400CycloheptanoneHCID 696866671-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one hydrochloride

Product 1

HCID 158711771-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)cycloheptane-carbonitrileYield 42.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 1-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane hydrochloride (578.8 mg, 2.16 mmol) and cycloheptanone (304 μl, 2.59 mmol) was added a solution of KCN (169 mg, 2.59 mmol) in water (1 ml) at room temperature. The reaction mixture was vigorously stirred at room temperature for 20 h. The precipitated white solid was collected by filtration, washed with water and hexane, and dried under vacuum at 50° C. for 1 h to afford 323 mg (42.4 %) of white powder.

Workup

  1. filtrationThe precipitated white solid was collected by filtration
  2. washwashed with water and hexane
  3. customdried under vacuum at 50° C. for 1 h

Sources & evidence

ORD record
ord-acb051045c044a428327e7e51299521e
Source dataset
uspto-grants-2002_10
Patent number
US06465478B1

Reaction notes

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