Sodium borohydride → 5-Methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline

HRID 419649노트

반응식

HRID 419649 반응식
[BH4-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([O:13][CH3:14])=[CH:6][C:5]=1[N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1>C1COCC1.CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:3][C:4]1[C:5]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:22][CH2:23][N:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:25][CH2:26]3)[CH2:17][CH2:16]2)=[CH:6][C:7]([O:13][CH3:14])=[C:8]([CH:9]=1)[NH2:10]

참가 물질

6

반응물 2

HCID 4311764Sodium borohydrideHCID 594529721-{1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine

생성물 1

HCID 594526035-Methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline수율 57.4%

시약·촉매·용매 3

HCID 11791229Dichloronickel;hexahydrate촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

Sodium borohydride (0.30 g, 7.93 mmol) was added in portions to a stirring suspension of 1-{1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine (1.09 g, 2.64 mmol) and Nickel(II)chloride hexahydrate (0.19 g, 0.8 mmol) in THF (10 mL) and MeOH (20 mL) at rt. The reaction mixture was allowed to stir at rt for 2 h and then it was concentrated in vacuo. The residue was taken up in DCM and passed through a bed of celite. The resultant filtrate was then concentrated onto silica gel and purified by flash chromatography to afford 5-methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (0.58 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.55 (s, 1H), 6.43 (s, 1H), 4.30 (s, 2H), 3.70 (s, 3H), 3.05-3.15 (m, 4H), 2.89-2.96 (m, 2H), 2.86 (s, 3H), 2.52-2.65 (m, 6H), 2.26-2.41 (m, 1H), 2.06 (s, 3H), 1.74-1.85 (m, 2H), 1.43-1.63 (m, 2H).

후처리

  1. concentrationit was concentrated in vacuo
  2. concentrationThe resultant filtrate was then concentrated onto silica gel
  3. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-953b4dc7bc28437b8abaf331e947f3cf
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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