Diisopropylethylamine → N-(5-Bromo-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

HRID 2064182

반응식

HRID 2064182 반응식
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4](F)[CH:3]=1.Cl.Cl.[O:15]1[CH2:20][CH2:19][CH:18]([N:21]2[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4]([NH:27][CH:24]2[CH2:23][CH2:22][N:21]([CH:18]3[CH2:19][CH2:20][O:15][CH2:16][CH2:17]3)[CH2:26][CH2:25]2)[CH:3]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 451567511-(Oxan-4-yl)piperidin-4-amine--hydrogen chloride (1/2)

생성물 1

HCID 59850147N-(5-Bromo-4-fluoro-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine수율 107.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
200 °C

실험 절차

A mixture of 4-bromo-2,5-difluoro-1-nitrobenzene (1 g, 4.2 mmol), 1-(tetrahydro-2H-pyran-4yl)piperidin-4-amine dihydrochloride salt (D40, 1.08 g, 4.2 mmol), and di-iso-propylethylamine (2.2 ml, 1.26 mmol) in dimethylformamide (10 ml) was heated in microwave reactor for 5 min at 200° C. The mixture was washed with water, then extracted with dichloromethane and the extract dried over MgSO4 and concentrated under vacuum. The crude material was purified on silica column (100 g of silica, ethyl acetate/methanol: 1.0% to 0%, 3CV; 2.0% to 100% 2CV 3. 100% to 100% 5CV) to leave 1.82 g (96%) of a mixture of title compound and an unknown impurity (˜3:1 by HPLC).

후처리

  1. washThe mixture was washed with water
  2. extractionextracted with dichloromethane
  3. dry with materialthe extract dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe crude material was purified on silica column (100 g of silica, ethyl acetate/methanol: 1.0% to 0%, 3CV; 2.0% to 100% 2CV 3. 100% to 100% 5CV)

출처 및 근거

ORD 기록
ord-afd837f064b7470e8672d0888b02859a
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288412B2

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