Methanol → 2-(Methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline

HRID 1014344노트

반응식

HRID 1014344 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.CO.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 598602551-(3-Methoxy-4-nitro-phenyl)-4-methylsulfonyl-piperazine

생성물 1

HCID 598602722-(Methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1-[3-(Methyloxy)-4-nitrophenyl]-4-(methylsulfonyl)piperazine (1.09 g, 3.46 mmol) was suspended in 5 mL THF and 10 mL MeOH in a 100 mL round bottom flask. NiCl2-6H2O (0.247 g, 1.04 mmol) was added, followed by slow addition of NaBH4 (0.392 g, 10.38 mmol). The reaction mixture was adsorbed on SiO2 and purified via column chromatography to afford 2-(methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline. (0.925 g, 3.24 mmol, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.91 (s, 3 H) 2.99-3.07 (m, 4 H) 3.19-3.27 (m, 4 H) 3.75 (s, 3 H) 4.28 (s, 2 H) 6.33 (dd, J=8.39, 2.43 Hz, 1 H) 6.49-6.58 (m, 2 H). ESIMS M+H)+=285.

후처리

  1. custompurified via column chromatography

출처 및 근거

ORD 기록
ord-0d39f6e85ff841e68ea5e7f37a57c34f
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

반응 노트

불러오는 중…