Diisopropylethylamine → 2,3-Dichloro-4-(4-fluoro-4-phenylpiperidin-1-yl)pyridine

HRID 1428494ノート

反応式

HRID 1428494 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6](I)[CH:5]=[CH:4][N:3]=1.Cl.[F:11][C:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CC#N>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([N:15]2[CH2:16][CH2:17][C:12]([F:11])([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:13][CH2:14]2)[CH:5]=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 448870382,3-Dichloro-4-iodopyridineHCID 459337594-Fluoro-4-phenylpiperidine hydrochloride

生成物 1

HCID 574595992,3-Dichloro-4-(4-fluoro-4-phenylpiperidin-1-yl)pyridine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
110 °C

実験手順

A mixture of D10 (2 g, 7.302 mmol), 4-fluoro-4-phenylpiperidine hydrochloride (2.048 g, 9.493 mmol) [C.A.S. 1056382-25-2] and DIPEA (5.055 ml, 29.209 mmol) in CH3CN (10 ml) was heated in a sealed tube at 110° C. for 16 h. The mixture was then treated with NaHCO3 (aqueous sat. solution). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel; Heptane/DCM from 4:1 up to 1:4 as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D18 (0.88 g, 37%) as a white solid.

後処理

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (silica gel; Heptane/DCM from 4:1 up to 1:4 as eluent)
  5. customThe desired fractions were collected
  6. concentrationconcentrated in vacuo
  7. customto yield intermediate compound

出典と根拠

ORDレコード
ord-e7c1bd25a4f34329bcb134e44a4f6f8b
出典データセット
uspto-grants-2015_01
特許番号
US08937060B2

反応ノート

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