Cyanogen Bromide → 1-Cyano-3-(4-fluorophenacyl)piperidine

HRID 1657822노트

반응식

HRID 1657822 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[O:10])[CH2:3]1.[N:18]#CBr>C1C=CC=CC=1>[C:1]([N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[O:10])[CH2:3]1)#[N:18]

참가 물질

4

반응물 2

HCID 10476Cyanogen BromideHCID 123645001-Methyl-3-(4-fluorophenacyl)piperidine

생성물 1

HCID 215303571-Cyano-3-(4-fluorophenacyl)piperidine

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

The above reaction scheme generally follows the procedure of E. L. Engelhardt, J. Med. Chem., 11, 325 (1968). Briefly, 1-methyl-3-(4-fluorophenacyl)piperidine in benzene solution is treated at essentially ambient temperature with excess cyanogen bromide under a nitrogen purge. Volatile materials are distilled under reduced pressure and the residue is dissolved in chloroform. The chloroform solution is washed, dried, and filtered. Distillation of the chloroform gives 1-cyano-3-(4-fluorophenacyl)piperidine. Hydrolysis of the cyano compound with hydrochloric acid-containing aqueous acetic acid gives the 1-carbamoyl derivative and the completely hydrolyzed and decarboxylated piperidine derivative (wherein the cyano group effectively is replaced with hydrogen). Increasing the amount of hydrochloric acid employed and increasing reaction time appear to favor complete hydrolysis and decarboxylation.

후처리

  1. customThe above reaction scheme
  2. custompurge
  3. distillationVolatile materials are distilled under reduced pressure
  4. dissolutionthe residue is dissolved in chloroform
  5. washThe chloroform solution is washed
  6. customdried
  7. filtrationfiltered
  8. distillationDistillation of the chloroform

출처 및 근거

ORD 기록
ord-564835b256f84cf58f410c53ec115ad9
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03962257

반응 노트

불러오는 중…