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

HRID 968255ノート

反応式

HRID 968255 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dda1260c9a0042ddbe2a6786afc022df
出典データセット
uspto-grants-2005_10
特許番号
US06958340B2

反応ノート

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