1-Methylpiperazine → HCID 23296274, compound

HRID 1953476Notes

Reaction equation

HRID 1953476 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11](=[O:17])[C:10]([C:18]1[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)[CH:25]=3)[N:22]=1)=[CH:9]2.[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>>[ClH:1].[ClH:1].[ClH:1].[CH3:16][N:12]1[C:13]2[C:8](=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:46]3[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]3)=[CH:15][CH:14]=2)[CH:9]=[C:10]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)[CH:25]=3)[N:22]=2)[C:11]1=[O:17]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 15481570HCID 15481570, compound

Product 1

HCID 23296274HCID 23296274, compoundYield 269.7%

Conditions

Temperature
120 °C

Procedure

A mixture of crude 6-[3-chloropropyl]oxy-1-methyl-3-{2-[3-(2-quinolylmethoxy)benzyl]tetrazolyl}quinolin-2-one (180 mg, 0.317 mmol) and N-methylpiperazine (127 mg, 1.27 mmol) was stirred under an argon flow at a bath temperature of 120° C. for 90 minutes. The reaction mixture was concentrated under reduced pressure, and purified through silica gel chromatography (developer: chloroform-methanol (20:1)). Fractions containing the target compound were collected, and concentrated under reduced pressure, to thereby obtain the free base of the title compound (180 mg, 0.285 mmol) as yellow oily matter. The thus-obtained free base was dissolved in methanol (2 ml), and a solution of hydrochloric acid (4N) in ethyl acetate (285 μl, 1.14 mmol) was added thereto. The mixture was crystallized from a methanol-diethylether mixture, to thereby obtain the trihydrochloride; i.e., the title compound, as yellow needles (143 mg, 0.203 mmol, 64.1%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified through silica gel chromatography (developer: chloroform-methanol (20:1))
  3. additionFractions containing the target compound
  4. customwere collected
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4921183e03834f2bae556f1d6080d385
Source dataset
uspto-grants-2000_09
Patent number
US06117886

Reaction notes

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