Hydrochloric Acid → HCID 58079414、化合物

HRID 1521464

反応式

HRID 1521464 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:10])N)[CH:5]=[CH:6][CH:7]=1.[N:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C:14](=O)[CH2:13][CH2:12]2.Cl>C(O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:13]3[CH2:12][N:11]4[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]4)[C:14]=3[N:8]([CH3:10])[C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 64203071-Azabicyclo[3.2.2]nonan-4-oneHCID 53401181HCID 53401181、化合物

生成物 1

HCID 58079414HCID 58079414、化合物収率 58%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

1-(3-Bromophenyl)-1-methylhydrazine (0.50 g, 2.5 mmol) and 1-azabicyclo[3.2.2]nonan-4-one (0.38 g, 2.7 mmol) were dissolved in isopropanol (4 mL), and concentrated aqueous HCl (0.8 mL) was added. The reaction mixture was heated to reflux for 18 h, concentrated and basified using 2 N NaOH. The aqueous layer was extracted with methylene chloride (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, 0%-100% solvent mixture B in methylene chloride; solvent mixture B=80:18:2 methylene chloride/methanol/concentrated ammonium hydroxide) to give the title compound (438 mg, 58%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 7.40 (d, J=2.0 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 7.16 (d, J=1.6 Hz, 1H), 4.25 (s, 2H), 3.61 (s, 3H), 3.30-3.24 (m, 3H), 3.14-3.08 (m, 2H), 2.02-1.99 (m, 4H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationconcentrated
  4. extractionThe aqueous layer was extracted with methylene chloride (3×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash column chromatography (silica gel, 0%-100% solvent mixture B in methylene chloride; solvent mixture B=80:18:2 methylene chloride/methanol/concentrated ammonium hydroxide)

出典と根拠

ORDレコード
ord-9dc1c232c2a24b8aa8507b1e3ac59762
出典データセット
uspto-grants-2015_07
特許番号
US09073925B2

関連ノート

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