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

HRID 1372410Notes

Reaction equation

HRID 1372410 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([CH:11]([CH3:15])C(O)=O)[C:3]1=2.[C:16](N1C=CN=C1)(N1C=CN=C1)=[O:17].[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:16](=[O:17])[CH2:15][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 68791479HCID 68791479, compound

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 3-(4-oxo-4,5,6,7,tetrahydro-1H-indol-3-yl-propionic acid (48 mmol) in 60 mL of dichloromethane was added 9.3 g (57.6 mmol) of carbonyldiimidazole. After stirring at room temperature for 2 hours, 5.3 mL (48 mmol) of 1-methylpiperazine and 8.4 mL (48 mmol) of N,N-diisopropylethylamine were added. The dark red reaction mixture was stirred at room temperature overnight. The reaction was poured into water and the organic layer washed with brine, dried and concentrated to give 8 g (57% yield) of 3-[3-(4-methyl-piperazin-1-yl)-3-oxo-propyl]-1,5,6,7-tetrahydro-indol-4-one. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.97 (br s, 1H, NH), 6.47 (d, 1H), 3.43 (m, 4H, 2×CH2), 2.67–2.75 (m, 4H, 2×CH2), 2.51 (m, 2H, CH2), 2.27 (m, 2H, CH2), 2.20 (m, 4H, 2×CH2), 2.15 (s, 3H, CH3), 1.97 (m, 2H, CH2). MS m/z 289 [M+].

Workup

  1. customThe dark red reaction mixture
  2. stirringwas stirred at room temperature overnight
  3. washthe organic layer washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8c8efa0ed63f4bfe87846d91f0b3075e
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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