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

HRID 345494ノート

反応式

HRID 345494 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f56639b255ec472db262e155f4c14e76
出典データセット
uspto-grants-1991_10
特許番号
US05057524

反応ノート

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