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

HRID 20811노트

반응식

HRID 20811 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 593477851-[Bis(phenylmethyl)amino]cyclopentanecarbonitrile

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9b1ab97345d4dc9918fcfef0393f96d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745642B2

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