Piperidine → 2-(Piperidin-1-ylmethyl)benzonitrile

HRID 1071450노트

반응식

HRID 1071450 반응식
[C:1]([C:3]1[C:4](Br)=[C:5](C)[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[C:17]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:11]1([CH2:17][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N:2])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 154691152-Bromo-3-methylbenzonitrile

생성물 1

HCID 150759152-(Piperidin-1-ylmethyl)benzonitrile수율 100%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 35 g (0.18 mole) of cyanobromotoluene and 16.18 g (0.19 mole) of piperidine in 300 mL of anhydrous DMF was treated with 73 g (0.5 mole) of K2CO3 at 50° C. for 2 hr. The reaction mixture was filtered through a plug of Celite, washed with 400 mL of ethyl acetate, and the filtrate was partitioned between ethyl acetate and ½ saturated brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, yielding 36 g (0.18 mole) 100% of 2-Piperidin-1-ylmethyl-benzonitrile. 1H NMR (300 MHz, CDCl3) 7.6 (m, 3H), 7.24 (m, 1H), 3.6 (s, 2H), 2.4 (m, 4H), 1.5 (m, 6H).

후처리

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. washwashed with 400 mL of ethyl acetate
  3. customthe filtrate was partitioned between ethyl acetate and ½ saturated brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f118407ce6b8442aae942a7111af4b67
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906075B2

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