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

HRID 24338Notes

Reaction equation

HRID 24338 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

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 962WaterSolventHCID 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-diisopropylethyl-amine 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-e7c2e9861ee948699180cbf1873816fc
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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