Water → (S)-2-(4-benzyl-1-(2-bromo-5-methylphenyl)piperazin-2-yl)ethanol

HRID 80518

반응식

HRID 80518 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1F.CC(C)([O-])C.[Na+].O>CS(C)=O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:19]2[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=2[Br:17])[C@@H:10]([CH2:14][CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 5732804-Bromo-3-fluorotolueneHCID 23395653(S)-2-(4-benzylpiperazin-2-yl)ethanolHCID 23676156Sodium t-butoxide

생성물 1

HCID 66769566(S)-2-(4-benzyl-1-(2-bromo-5-methylphenyl)piperazin-2-yl)ethanol

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (S)-2-(4-benzylpiperazin-2-yl)ethanol (150 mg, 0.681 mmol) and 1-bromo-2-fluoro-4-methylbenzene (167 mg, 885 mmol) in dimethyl sulfoxide (5 mL) was added sodium tert-butoxide (164 mg, 1.70 mmol). The reaction mixture was allowed to stir for 16 hours at room temperature before addition of water and ethyl acetate. The organic layer was separated and concentrated onto silica gel. Purification via flash chromatography (0-30% methanol/dichloromethane) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.40 (d, J=7.80 Hz, 1H), 7.18-7.35 (m, 5H) 6.92 (d, J=1.36 Hz, 1H), 6.65-6.73 (m, 1H), 4.08 (t, J=6.44 Hz, 2H), 3.36-3.51 (m, 2H), 2.55-2.89 (m, 6H),1.87-1.99 (m, 1H), 1.68-1.77 (m, 2H); MS (APCI+) m/z 389, 391 (M+H)+.

후처리

  1. customThe organic layer was separated
  2. concentrationconcentrated onto silica gel
  3. customPurification via flash chromatography (0-30% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-b21ae1bf85e44c2dadab4c427ba14d1c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846663B2

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