Water → 6-Bromo-8-piperazin-1-yl-quinoline

HRID 428541

反応式

HRID 428541 の反応式
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([Br:24])[CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClCCOC(Cl)=O.ClC(OC=C)=O.O>ClC(Cl)C>[Br:24][C:16]1[CH:17]=[C:18]2[C:23](=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:15]=1)[N:22]=[CH:21][CH:20]=[CH:19]2

参加物

6

反応物 4

HCID 962WaterHCID 123052-Chloroethyl chloroformateHCID 78808Vinyl chloroformateHCID 184140798-(4-Benzyl-piperazin-1-yl)-6-bromo-quinoline

生成物 1

HCID 184140636-Bromo-8-piperazin-1-yl-quinoline収率 84%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 8-(4-benzyl-piperazin-1-yl)-6-bromo-quinoline (1.6 g, 4.2 mmol) in dichloroethane (50 mL) under a N2 atmosphere was added chloroethylchloroformate (1.26 mL, 12.6 mmol) and the reaction mixture was heated at 80° C. for 4 hours, and at ambient temperaure overnight. No reaction was observed by TLC, therefore vinyl chloroformate (0.35 mL, 6.3 mmol) was added and the reaction was heated at 80° C. for another 4 hours. The cooled reaction was poured into H2O and extracted into CH2Cl2 (2×100 mL) and EtOAc (100 mL). The organic fractions were combined, dried over Na2SO4, and left in EtOAc overnight. The organic layer was concentrated and purified by column chromatography 10%MeOH/CH2C2+NH4OH) affording 1.03 g (84%) of a brown foam. MS(+)APCI m/z 292 [M+H]+.

後処理

  1. temperaturethe reaction was heated at 80° C. for another 4 hours
  2. customThe cooled reaction
  3. extractionextracted into CH2Cl2 (2×100 mL) and EtOAc (100 mL)
  4. dry with materialdried over Na2SO4
  5. waitleft in EtOAc overnight
  6. concentrationThe organic layer was concentrated
  7. custompurified by column chromatography 10%MeOH/CH2C2+NH4OH)

出典と根拠

ORDレコード
ord-f89bd88f9d2248a5ae5909fa844d6f8d
出典データセット
uspto-grants-2001_11
特許番号
US06313126B1

関連ノート

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