4-(piperazin-1-yl)-1H-indole → (R)-1-(4-indolyl)-4-[2-methyl-2-(2-pyridinylamino)ethyl]piperazine

HRID 368703

反応式

HRID 368703 の反応式
[CH3:1][C@@H:2]1[CH2:6]OS(=O)(=O)[N:3]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[N:15]1([C:21]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[CH:24][NH:25]3)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(#N)C>[NH:25]1[C:26]2[C:22](=[C:21]([N:15]3[CH2:20][CH2:19][N:18]([CH2:6][C@@H:2]([CH3:1])[NH:3][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=4)[CH2:17][CH2:16]3)[CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:24]1

参加物

4

反応物 2

HCID 5945904-(piperazin-1-yl)-1H-indoleHCID 22863100(R)-4-methyl-3-pyridin-2-yl[1,2,3]oxathiazolidine-2,2-dioxide

生成物 1

HCID 53956483(R)-1-(4-indolyl)-4-[2-methyl-2-(2-pyridinylamino)ethyl]piperazine収率 67.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

A solution of (R)4-methyl-3-pyridin-2-yl-[1,2,3]-oxathiazolidine-2,2-dioxide (4.04 g 0.019 moles) prepared according to Example 1 and 4-piperazinoindole (3.80 g 0.019 moles) in acetonitrile (200 ml) was heated to 60° C. for 0.5 h then evaporated in vacuo. The residue was taken up into dilute hydrochloric acid (100 ml), warmed to 60° C. for 0.5 h, cooled, washed with ethyl acetate (2×100 ml), made basic with potassium carbonate, extracted into dichloromethane (3×100 ml), dried (MgSO4) then evaporated in vacuo to give a brown glass. This was purified on a silica column eluting with 10% propan-2-ol in dichloromethane to give (R)-1-(4-indolyl)-4-[2-methyl-2-(2-pyridinylamino)ethyl]piperazine (4.3 g) as a clear glass.

後処理

  1. customthen evaporated in vacuo
  2. temperaturewarmed to 60° C. for 0.5 h
  3. temperaturecooled
  4. washwashed with ethyl acetate (2×100 ml)
  5. extractionextracted into dichloromethane (3×100 ml)
  6. dry with materialdried (MgSO4)
  7. customthen evaporated in vacuo
  8. customto give a brown glass
  9. customThis was purified on a silica column
  10. washeluting with 10% propan-2-ol in dichloromethane

出典と根拠

ORDレコード
ord-b1a18246ee5b4cd1858aa1405bab7433
出典データセット
uspto-grants-2000_10
特許番号
US06133449

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