Hydrochloric Acid → HCID 66711152、化合物

HRID 1262344ノート

反応式

HRID 1262344 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].Cl.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:35])[CH2:33]Br)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>O>[C:19]([O:23][C:24]([N:26]1[CH2:27][CH2:28][N:29]([C:32](=[O:35])[CH2:33][N:15]2[CH2:14][CH:13]=[C:12]([C:5]3[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:17][CH2:16]2)[CH2:30][CH2:31]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

参加物

7

反応物 5

HCID 313Hydrochloric Acid2 回HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylateHCID 569460604-(3-Methoxy-4-nitrophenyl)-1,2,3,6-tetrahydropyridine

生成物 1

HCID 66711152HCID 66711152、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Into a 1-Neck round-bottom flask was added 4-(3-Methoxy-4-nitro-phenyl)-1,2,3,6-tetrahydro-pyridine; hydrochloride (364 mg, 1.34 mmol) (generated by 4N HCl treatment of the 450 mg of BOC precursor for 1 h), 4-(2-Bromo-acetyl)-piperazine-1-carboxylic acid tert-butyl ester (413.0 mg, 1.345 mmol) and cesium carbonate (1095 mg, 3.362 mmol) in acetonitrile (10 mL, 200 mmol). The reaction was stirred overnight at reflux. The reaction mixture was cooled to RT, diluted with water and was extracted (twice) from EtOAc. Combined organic was washed with brine and was dried over MgSO4. After solvent evaporation and flash chromatography (ISCO, EtOAC: MeOH 98:2), the product, 4-{2-[4-(3-Methoxy-4-nitro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetyl}-piperazine-1-carboxylic acid tert-butyl ester, was isolated as a gum/solid (301 mg, 49%). NMR 1H (DMSO-d6)-7.86 (d, 1H, J=8.54 Hz), 7.29 (s, 1H), 7.17 (d, 1H, J=8.58 Hz), 6.44 (s, 1H), 3.96 (s, 3H), 3.52 (br s, 2H), 3.44 (br s, 2H), 3.32 m with the water peak, 8H), 3.30 (m, 2H).

後処理

  1. temperatureat reflux
  2. extractionwas extracted (twice) from EtOAc
  3. washCombined organic was washed with brine
  4. dry with materialwas dried over MgSO4
  5. customAfter solvent evaporation and flash chromatography (ISCO, EtOAC: MeOH 98:2)

出典と根拠

ORDレコード
ord-03cb50772eba403ca75741bede0a0275
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

反応ノート

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