Cyclopentanone → 1-[Bis(phenylmethyl)amino]cyclopentanecarbonitrile

HRID 20811Notes

Reaction equation

HRID 20811 reaction equation
Cl.[CH2:2]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18]1.[C-:23]#[N:24].[K+]>C(O)C.O>[C:11]1([CH2:10][N:9]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:17]2([C:23]#[N:24])[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 8452CyclopentanoneHCID 9032Potassium CyanideHCID 13000629Benzenemethanamine, N-(phenylmethyl)-, hydrochloride (1:1)

Product 1

HCID 593477851-[Bis(phenylmethyl)amino]cyclopentanecarbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

To an ice-cooled suspension of dibenzylamine hydrochloride (13.5 g; 0.058 mol) and cyclopentanone (4.86 g; 0.058 mol) in 25% ethanol in water (100 ml) was added ethanol (60 ml) and a solution of potassium cyanide (3.78 g; 0.058 mol) in water (35 ml) dropwise over 20 minutes with stirring. After 6 days the reaction mixture was extracted with ethyl acetate, washed with sodium bicarbonate solution, dried (Na2SO4) and evaporated in vacuo to afford the title compound as an off white solid (8.32 g, 49%). 1H NMR (CDCl3) δ: 1.72 (6H, m), 2.12 (2H, m), 3.78 (4H, m), 7.1-7.3 (10H, m); Mass Spectrum (Electrospray LC/MS): Found 264 (MH+−HCN). C20H22N2 requires 290. Ret. time 1.88 min.

Workup

  1. extractionAfter 6 days the reaction mixture was extracted with ethyl acetate
  2. washwashed with sodium bicarbonate solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e9b1ab97345d4dc9918fcfef0393f96d
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

Loading…