4-(2-Pyrimidinyl)-1-piperazinebutanamine → 3-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-8-oxa-3-azabicyclo[3.2.1]octane-2,4-dione

HRID 1253259ノート

反応式

HRID 1253259 の反応式
[O:1]1[CH:5]2[C:6]([O:8][C:9](=[O:10])[CH:2]1[CH2:3][CH2:4]2)=O.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:18][CH2:17]1>C1(C)C=CC=CC=1>[N:23]1[CH:24]=[CH:25][CH:26]=[N:27][C:22]=1[N:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:11]2[C:6](=[O:8])[CH:5]3[O:1][CH:2]([CH2:3][CH2:4]3)[C:9]2=[O:10])[CH2:17][CH2:18]1

参加物

4

反応物 2

HCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamineHCID 134257993,8-Dioxabicyclo[3.2.1]octane-2,4-dione

生成物 1

HCID 141563573-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl]-8-oxa-3-azabicyclo[3.2.1]octane-2,4-dione

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Tetrahydrofuran-2,5-dicarboxylic anhydride (1.5 g., 10 mmole) was dissolved in 150 ml. of toluene in a 500 ml. round bottom flask equipped with a Dean-Stark trap and condenser. 1-(4-Aminobutyl)-4-(2-pyrimidinyl)piperazine (2.59 g., 11 mmole) was added and the mixture was refluxed for 24 hours. When the analysis failed to detect the expected product, the solvent was removed in vacuum and replaced with xylene. Reflux was continued for 48 hours. The solvent was then removed in vacuum and the residue column chromatographed on 100 g. of silica gel using a gradient elution from pure chloroform to 5% ethanol/chloroform. The relevant fractions were combined and concentrated in vacuum and the product crystallized from isopropanol with the addition of 4N HCl/isopropanol. 1.2 Grams of the title compound was obtained as the dihydrochloride; m.p. 221°-222° C.

後処理

  1. customround bottom flask equipped with a Dean-Stark trap and condenser
  2. temperaturethe mixture was refluxed for 24 hours

出典と根拠

ORDレコード
ord-391618eea526461f94cb8ae9bc43a513
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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