1-Methylpiperazine → 1-{2,2-Dimethyl-3-[4-(4-chlorophenyl)piperazin-1-yl]-3-oxopropyl}-4-methylpiperazine

HRID 417989ノート

反応式

HRID 417989 の反応式
Br[CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH2:3]1.[CH3:15][C:16]([CH3:20])([CH3:19])[CH:17]=[O:18].[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CN1CCCC1=O>[CH3:15][C:16]([CH3:20])([C:17]([N:7]1[CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1)=[O:18])[CH2:19][N:25]1[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]1

参加物

4

反応物 2

HCID 531671-MethylpiperazineHCID 866357763-Bromo-1-(4-chlorophenyl)piperazine 2,2-dimethylpropan-1-one

生成物 1

HCID 579554691-{2,2-Dimethyl-3-[4-(4-chlorophenyl)piperazin-1-yl]-3-oxopropyl}-4-methylpiperazine収率 36.4%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
200 °C

実験手順

3-Bromo-1-(4-chlorophenyl)piperazine-2,2-dimethylpropan-1-one (0.87 g, 2.43 mmol) was dissolved in N-methylpyrrolidinone (3 mL). N-Methylpiperazine (0.54 mL, 4.85 mmol) was added and the reaction mixture was heated at 200° C. for 15 minutes in a Biotage Initiator microwave at normal absorption. The reaction mixture was purified by reverse phase column chromatography (gradient eluting with MeOH in water, with 1% formic acid in each solvent, 0-30%). The resulting residue was dissolved in DCM (100 mL) and stirred with solid K2CO3 for 20 minutes, filtered and concentrated ill vacuo, to give a pale brown oil which was recrystallised from heptane to give 1-{2,2-dimethyl-3-[4-(4-chlorophenyl)piperazin-1-yl]-3-oxopropyl}-4-methylpiperazine (335 mg, 36.4%) as a white solid.

後処理

  1. customThe reaction mixture was purified by reverse phase column chromatography (gradient
  2. washeluting with MeOH in water, with 1% formic acid in each solvent, 0-30%)
  3. dissolutionThe resulting residue was dissolved in DCM (100 mL)
  4. filtrationfiltered
  5. concentrationconcentrated ill vacuo
  6. customto give a pale brown oil which
  7. customwas recrystallised from heptane

出典と根拠

ORDレコード
ord-28e102905237482f8250978e55f8f63a
出典データセット
uspto-grants-2012_01
特許番号
US08093248B2

反応ノート

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