4-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amine → 3-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-9-oxa-3-azabicyclo[3.3.1]nonane-2,4-dione

HRID 1253268ノート

反応式

HRID 1253268 の反応式
[O:1]1[CH:6]2[C:7]([O:9][C:10](=[O:11])[CH:2]1[CH2:3][CH2:4][CH2:5]2)=O.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[N:27][CH:26]=[C:25]([Cl:29])[N:24]=2)[CH2:19][CH2:18]1>C(Cl)Cl>[Cl:29][C:25]1[N:24]=[C:23]([N:20]2[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:12]3[C:7](=[O:9])[CH:6]4[O:1][CH:2]([CH2:3][CH2:4][CH2:5]4)[C:10]3=[O:11])[CH2:22][CH2:21]2)[CH:28]=[N:27][CH:26]=1

参加物

4

反応物 2

HCID 140865264-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amineHCID 542819683,9-Dioxabicyclo[3.3.1]nonane-2,4-dione

生成物 1

HCID 141563773-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-9-oxa-3-azabicyclo[3.3.1]nonane-2,4-dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Tetrahydropyran-2,6-dicarboxylic anhydride (3.12 g., 20 mmole) and 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)piperazine (5.94 g., 22 mmole) were combined in 200 ml. of methylene chloride and stirred for 30 minutes at room temperature. The solvent was removed in vacuum and replaced with 350 ml. of xylene. The mixture was refluxed for 50 hours with water removal via a Dean-Stark trap. The xylene was evaporated and the residue was filtered through 75 g. of silica gel with 2% ethanol/chloroform. The product was concentrated in vacuum and crystallized from isopropanol with the addition of 4N isopropanolic HCl. A second recrystallization from methanol gave 4.18 g. of the title compound as the monohydrochloride; m.p. 252°-253° C.

後処理

  1. customThe solvent was removed in vacuum
  2. temperatureThe mixture was refluxed for 50 hours with water removal via a Dean-Stark trap
  3. customThe xylene was evaporated
  4. filtrationthe residue was filtered through 75 g
  5. concentrationThe product was concentrated in vacuum
  6. customcrystallized from isopropanol with the addition of 4N isopropanolic HCl
  7. customA second recrystallization from methanol
  8. customgave 4.18 g

出典と根拠

ORDレコード
ord-f263cbc2a829490da1aeec851e975a14
出典データセット
uspto-grants-1988_05
特許番号
US04748240

反応ノート

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