Acetonitrile → 4-[3-[4-(6-Fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]propoxy]-3-hydroxyphenyl ethanone

HRID 370206ノート

反応式

HRID 370206 の反応式
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][S:8][C:4]=2[CH:3]=1.Cl[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][C:23]=1[OH:31].C([O-])(O)=O.[Na+].CC#N>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][C:23]=4[OH:31])[CH2:13][CH2:14]3)=[N:7][S:8][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 103765071-(4-(3-Chloropropoxy)-3-hydroxyphenyl]ethanoneHCID 185049766-Fluoro-3-(4-piperidinyl)-1,2-benzisothiazole

生成物 1

HCID 219600124-[3-[4-(6-Fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]propoxy]-3-hydroxyphenyl ethanone収率 97%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (2.4 g, 10.1 mmol), 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (2.5 g, 11.1 mmol), NaHCO3, (0.94 g, 11.1 mmol), KI (100 mg) and CH3CN (100 ml) was stirred at reflux under N2 for 65 hours. The cooled reaction was poured into H2O and the aqueous mixture was extracted with EtOAc. The EtOAc extract was washed with H2O (1×) and brine (3×) and after drying with MgSO4 the solvent was evaporated to give 4.2 g of a dark solid. Three consecutive recrystallizations from EtOH provided 2.1 g (48%) of glittery beige crystals m.p.=135-137° C.

後処理

  1. temperatureat reflux under N2 for 65 hours
  2. customThe cooled reaction
  3. extractionthe aqueous mixture was extracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with H2O (1×) and brine (3×)
  6. dry with materialafter drying with MgSO4 the solvent
  7. customwas evaporated

出典と根拠

ORDレコード
ord-833d5525991249338cd423bf0d3955ad
出典データセット
uspto-grants-2000_10
特許番号
US06140345

反応ノート

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