Potassium Iodide → 4-[Bis(4-fluorophenyl)hydroxymethyl]-N-methyl-1-piperidinepentanamide

HRID 345494노트

반응식

HRID 345494 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:30][CH3:31])=[O:29].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O.C(OCC)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:9])[CH:10]2[CH2:11][CH2:12][N:13]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:30][CH3:31])=[O:29])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 199923245-Chloro-N-methylpentanamide

생성물 1

HCID 199922774-[Bis(4-fluorophenyl)hydroxymethyl]-N-methyl-1-piperidinepentanamide수율 71%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 6.1 g (0.020 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 3.7 g (0.025 mole) of 5-chloro-N-methylpentanamide, 8.5 g (0.080 mole) of anhydrous sodium carbonate and 0.4 g (0.002 mole) of potassium iodide in 100 mL of N,N-dimethylformamide was heated on a steam bath for 24 h. The mixture was poured into 1.5 L of water and extracted twice with 500 ml portions of ethyl acetate. The ethyl acetate portions were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a golden oil. The oil was dissolved in ethyl ether and allowed to stand, whereupon a white solid precipitated. The solid was collected by filtration, and recrystallized from ethyl ether to yield 5.9 g (71%) of white solid, mp 130°-131° C.

후처리

  1. extractionextracted twice with 500 ml portions of ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a golden oil
  6. customprecipitated
  7. filtrationThe solid was collected by filtration
  8. customrecrystallized from ethyl ether

출처 및 근거

ORD 기록
ord-f56639b255ec472db262e155f4c14e76
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057524

반응 노트

불러오는 중…