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1-Methylpiperazine → 3-[3-(4-Methylpiperazin-1-yl)-3-oxo-propyl]-1,5,6,7-tetrahydroindol-4-one

HRID 1860738
Notes
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Reaction equation

HRID 1860738 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([CH2:11][CH2:12][C:13]([OH:15])=O)[C:3]1=2.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(N(CC)C(C)C)(C)C>ClCCl.O>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([C:13](=[O:15])[CH2:12][CH2:11][C:4]2[C:3]3[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=3[NH:6][CH:5]=2)[CH2:31][CH2:30]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 158327213-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid

Product 1

HCID 225710693-[3-(4-Methylpiperazin-1-yl)-3-oxo-propyl]-1,5,6,7-tetrahydroindol-4-oneYield 57.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 10 g of the product of step 1 (48 mmol) in dichloromethane(60 mL) was added 9.3 g (57.6 mmol) of 1,1′-carbonyldiimidazole. The mixture was stirred at room temperature for 2 hours and then 5.3 mL (48 mmol) 1-methylpiperazine and 8.4 mL (48 mmol) N,N-diisopropylethylamine was added. The dark red reaction mixture was then stirred at room temperature overnight. The reaction was then poured into water, the organic layer separated and washed with brine, dried and concentrated to give 8 g (57%) of 3-[3-(4-methylpiperazin-1-yl)-3-oxo-propyl]-1,5,6,7-tetrahydroindol-4-one.

Workup

  1. customThe dark red reaction mixture
  2. stirringwas then stirred at room temperature overnight
  3. customthe organic layer separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be9dd979aca44122a251b4af1952d89b
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06531502B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes