Acetic Acid → 1-{4-[(3-Nitrophenyl)methyl]piperazin-1-yl}ethan-1-one

HRID 968255노트

반응식

HRID 968255 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[C:12]([N:15]1[CH2:20][CH2:19][N:18]([CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 837951-AcetylpiperazineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 222884131-{4-[(3-Nitrophenyl)methyl]piperazin-1-yl}ethan-1-one

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

3-Nitrobenzaldehyde (2.04 g, 13.5 mmol) was dissolved in 50 ml 1,2-dichloroethane. 1-Acetylpiperazine 1.90 g, 14.9 mmol) and sodium triacetoxyborohydride (3.15 g, 14.9 mmol) were added followed by the addition of 0.100 ml of acetic acid. The reaction was allowed to proceed overnight (18 hours) and was then quenched with half-saturated NaHCO3 (aq). The mixture was extracted 3× with DCM and the organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (eluting with 95:5 DCM/MeOH) to afford 1-acetyl-4-(3-nitrobenzyl)piperazine (5-2). 1H NMR (300 MHz, CDCl3) δ 8.22 (s, 1H), 8.13 (dd, J=1.2, 8.3 Hz, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.50 (t, J=7.9 Hz, 1H), 3.63 (t, J=5.2 Hz, 2H), 3.61 (s, 2H), 3.48 (t, J=4.8 Hz, 2H), 2.44 (m, 4H), 2.08 (s, 3H).

후처리

  1. custom(18 hours) and was then quenched with half-saturated NaHCO3 (aq)
  2. extractionThe mixture was extracted 3× with DCM
  3. dry with materialthe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (eluting with 95:5 DCM/MeOH)

출처 및 근거

ORD 기록
ord-dda1260c9a0042ddbe2a6786afc022df
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958340B2

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