Formaldehyde → 4-(6-Chloronaphthalene-2-sulfonyl)-1-{methyl[1-(4-pyridyl)-4-piperidinyl]amino}-2-piperazinone

HRID 2086282Notes

Reaction equation

HRID 2086282 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[O:34])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[OH-].[Na+].[CH2:37]=O>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([N:21]([CH3:37])[CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[O:34])[CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 178254104-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone

Product 1

HCID 227271244-(6-Chloronaphthalene-2-sulfonyl)-1-{methyl[1-(4-pyridyl)-4-piperidinyl]amino}-2-piperazinone

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(Method C) 4-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone (90 mg) was dissolved in a 37% aqueous solution of formaldehyde (2.9 ml) and formic acid (1.4 ml) and refluxed for 15 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 obtained was purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) to obtain the title compound (38 mg) as colorless crystals.

Workup

  1. temperaturerefluxed for 15 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customwas purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)

Sources & evidence

ORD record
ord-b211280cbbcc46f4b3e178c1132357bf
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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