1-Methylpiperazine → HCID 18668777, compound

HRID 1058626Notes

Reaction equation

HRID 1058626 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C(=O)([O-])O.[Na+]>>[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([C:2]2[C:11]3[N:12]=[C:13]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:14]([CH2:15][CH2:16][CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19][CH2:18]4)[C:10]=3[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=2)[CH2:39][CH2:38]1

Participants

4

Reactant 3

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 18668762HCID 18668762, compound

Product 1

HCID 18668777HCID 18668777, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 0.80 g of tert-butyl 4-[2-(4-chloro-2-phenyl-1H-imidazo-[4,5-c]quinolin-1-yl)ethyl]-1-piperidinecarboxylate and 1 ml of N-methylpiperazine was stirred at 80° C. for 6 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was dried, and the solvent was evaporated. The residue was purified by alumina column chromatography using ethyl acetate—n-heptane (1:3 to 1:1) as eluting solvents, and washed with a mixture of diisopropyl ether and n-heptane to give 0.74 g of colorless crystals. Recrystallization from ethyl acetate gave colorless needles having the melting point of from 140 to 141° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was dried
  3. customthe solvent was evaporated
  4. customThe residue was purified by alumina column chromatography
  5. washas eluting solvents
  6. washwashed with a mixture of diisopropyl ether and n-heptane

Sources & evidence

ORD record
ord-e66dc32f85a24e8fb521505f2441a919
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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