Formaldehyde → HCID 22727143, compound

HRID 2086316Notes

Reaction equation

HRID 2086316 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][N:14]3[CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH:29]=[CH2:30])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH2:16][C:15]3=[O:31])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:34]=O>C(O)=O>[CH3:34][N:13]([CH:10]1[CH2:11][CH2:12][N:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:8][CH2:9]1)[N:14]1[CH2:19][CH2:18][N:17]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([CH:29]=[CH2:30])=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH2:16][C:15]1=[O:31]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 22727300HCID 22727300, compound

Product 1

HCID 22727143HCID 22727143, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-{[1-(4-pyridinyl)-4-piperidinyl]amino}-4-(4-vinylbenzenesulfonyl)-2-piperazinone (180 mg) was dissolved in a 37% aqueous solution of formaldehyde (11 ml and formic acid (5 ml) and refluxed for 2 hours. The reaction mixture was cooled and made alkaline by adding an aqueous solution of sodium hydroxide, extracted with dichloromethane, dried and concentrated. The residue was purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) and crystallized from ether to obtain the title compound (139 mg, 75%) as colorless crystals.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)
  7. customcrystallized from ether

Sources & evidence

ORD record
ord-1954233244464179a8501559f92da641
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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