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

HRID 587633노트

반응식

HRID 587633 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1a905621b0224dcabcf1ade3d87e35f3
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226930B2

반응 노트

불러오는 중…