Sodium hydride → N-acetyl-4-(2-phenylallyloxy)piperidine

HRID 1732348노트

반응식

HRID 1732348 반응식
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH2:16]>CN(C)C=O.O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH2:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 234998(3-bromoprop-1-en-2-yl)benzeneHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

생성물 1

HCID 20306014N-acetyl-4-(2-phenylallyloxy)piperidine수율 101.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매3회

실험 절차

N-Acetyl-4-hydroxypiperidine (13.6 g.) in dimethylformamide (50 ml.) was added dropwise to a stirred suspension of sodium hydride (10 g. 50% dispersion in mineral oil) in dimethylformamide (50 ml.) under nitrogen. The mixture was stirred at room temperature for 3 hours then α-(bromomethyl)styrene (20 g.) in dimethylformamide (50 ml.) was added dropwise. The mixture was stirred at room temperature for 4 hours, then diluted with water and extracted with chloroform (3×200 ml.). The combined chloroform extracts were dried (Na2SO4), evaporated in vacuo, and distilled to give N-acetyl-4-(2-phenylallyloxy)piperidine (25 g.), b.p. 170°-180° C./0.3 mm. with an n.m.r. spectrum in accordance with this structure.

후처리

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. extractionextracted with chloroform (3×200 ml.)
  3. dry with materialThe combined chloroform extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. distillationdistilled

출처 및 근거

ORD 기록
ord-4a43641a25d943c284d24cd6cf6312f7
출처 데이터셋
uspto-grants-1980_12
특허 번호
US04237138

반응 노트

불러오는 중…