Sodium Carbonate → (S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine

HRID 1460473ノート

反応式

HRID 1460473 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][S:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29]Br)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.[I-].[Na+]>[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29][N:1]2[CH2:5][CH2:4][CH2:3][C@H:2]2[CH2:6][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][S:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)=[CH:26][CH:25]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 22841647(S)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]-thiazepine

生成物 1

HCID 9824029(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine収率 62%

試薬・触媒・溶媒 2

HCID 5238Sodium Iodide触媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of (S)-5,11-dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine (see Preparations 13 and 14) (2.8 g), 4-methoxyphenethyl bromide (2.6 g), sodium carbonate (1.30 g) and sodium iodide (50 mg) in acetonitrile (75 ml) was heated under reflux for 16 hours, evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was washed with water, dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, performing a gradient elution using initially dichloromethane as eluant and changing to dichloromethane/saturated methanolic ammonia (98:2). The appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil, (2.5 g, 62%).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customevaporated under reduced pressure
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel
  9. washa gradient elution
  10. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-5c56bcb1c7f94f929b357644e9bd0909
出典データセット
uspto-grants-1991_12
特許番号
US05071844

反応ノート

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