1-Methylpiperazine → HCID 18698346、化合物

HRID 2289826ノート

反応式

HRID 2289826 の反応式
Cl.Cl.[NH2:3][C:4]1([C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5]1.O.OC1C2N=NNC=2C=CC=1.[C:29]([O:33][C:34](NC1(C(O)=O)CCCC1)=[O:35])([CH3:32])([CH3:31])[CH3:30].CN1CCNCC1>CN(C=O)C>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C:9]([C:4]2([NH:3][C:34](=[O:35])[O:33][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:8][CH2:7][CH2:6][CH2:5]2)=[O:10])[CH2:12][CH2:13]1

参加物

6

反応物 4

HCID 531671-MethylpiperazineHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acidHCID 186982131-(4-methylpiperazine-1-carbonyl)cyclopentan-1-amine dihydrochlorideHCID 178526939HCID 178526939、化合物

生成物 1

HCID 18698346HCID 18698346、化合物収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(1-Aminocyclopentyl)(4-methyl-1-piperazinyl)methanone dihydrochloride ##STR204## 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.49 g, 13.0 mmol) was added portionwise to a cooled (4° C.) solution of hydroxybenzotriazole hydrate (1.49 g, 11.0 mmol) and 1-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (2.29 g, 10.0 mmol) in DMF (15 ml), and the mixture stirred for 30 min. N-Methylpiperazine (1.10 g, 11.0 mmol) was added, the reaction stirred for 30 min. allowed to warm to room temperature and stirring continued for a further 17 h. The reaction mixture was evaporated in vacuo, and the residual yellow oil partitioned between saturated Na2CO3 solution and EtOAc. The layers were separated, the aqueous phase extracted with EtOAc, and the combined organic solutions dried (MgSO4) and concentrated in vacuo. The residual solid was pre-adsorbed onto silica gel and purified by column chromatography upon silica gel using an elution gradient of CH2Cl2 -MeOH-0.880 NH3 (97.5:2.5:0.25 to 90:10:1) and triturated with Et2O to afford tert-butyl 1-[(4-methyl-1-piperazinyl)carbonyl]cyclopentylcarbamate (2.31 g, 7.4 mmol) as a crystalline solid.

後処理

  1. stirringthe reaction stirred for 30 min.
  2. stirringstirring
  3. waitcontinued for a further 17 h
  4. customThe reaction mixture was evaporated in vacuo
  5. customthe residual yellow oil partitioned between saturated Na2CO3 solution and EtOAc
  6. customThe layers were separated
  7. extractionthe aqueous phase extracted with EtOAc
  8. dry with materialthe combined organic solutions dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. custompurified by column chromatography upon silica gel using an elution gradient of CH2Cl2 -MeOH-0
  11. custom880 NH3 (97.5:2.5:0.25 to 90:10:1) and triturated with Et2O

出典と根拠

ORDレコード
ord-df8ba963088a4a53ae0a9f1c9eff417a
出典データセット
uspto-grants-2000_07
特許番号
US06093731

反応ノート

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