HCID 22727134, compound → HCID 22727135, compound

HRID 2086287Notes

Reaction equation

HRID 2086287 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14]([N:17]1[CH2:22][CH:21]([CH3:23])[N:20]([NH:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)[C:19](=[O:37])[CH2:18]1)(=[O:16])=[O:15])[CH:8]=[CH:7]2>C(Cl)Cl>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14]([N:17]1[CH2:22][CH:21]([CH3:23])[N:20]([NH:24][CH:25]3[CH2:26][CH2:27][N:28]([C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[CH2:29][CH2:30]3)[C:19](=[O:37])[CH2:18]1)(=[O:15])=[O:16])[CH:8]=[CH:7]2

Participants

3

Reactant 1

HCID 22727134HCID 22727134, compound

Product 1

HCID 22727135HCID 22727135, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(6-Chloro-2-naphthyl)sulfonyl]-6-methyl-1-[[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinone dihydrochloride (0.63 g) was dissolved in methylene chloride (20 ml) and saturated aqueous sodium bicarbonate (20 ml) and the phases were separated. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to obtain 4-[(6-chloro-2-naphthyl)sulfonyl]-6-methyl-1-[[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinone. This material was dissolved in a 37% aqueous solution of formaldehyde (8.0 ml) and formic acid (4.1 ml) and refluxed for 2 hours. The reaction mixture was cooled, made alkaline by adding a 1N aqueous solution of sodium hydroxide, extracted with dichloromethane, dried and concentrated. The residue thus obtained was purified by a column chromatography on a silica gel (ethyl acetate: methanol=10:1) to obtain the title compound (370 mg) as colorless crystals.

Workup

  1. customsaturated aqueous sodium bicarbonate (20 ml) and the phases were separated
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a08f8e83f8141ec88c9fd0eb5f7f440
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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