1-(Pyridin-4-yl)piperidin-4-one → 4-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-piperazinone

HRID 2086272Notes

Reaction equation

HRID 2086272 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:21])[CH:17]=3)[CH:12]=2)(=[O:10])=[O:9])[CH2:4][C:3]1=[O:22].[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]2)=[CH:25][CH:24]=1>C(O)C>[Cl:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:8]([N:5]1[CH2:6][CH2:7][N:2]([N:1]=[C:32]3[CH2:31][CH2:30][N:29]([C:26]4[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=4)[CH2:34][CH2:33]3)[C:3](=[O:22])[CH2:4]1)(=[O:9])=[O:10])[CH:20]=[CH:19]2

Participants

4

Reactant 2

HCID 113327931-(Pyridin-4-yl)piperidin-4-oneHCID 227270831-Amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

Product 1

HCID 695457164-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-piperazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(tert-Butoxycarbonylamino)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (575 mg) was combined with methanol (4 ml) and a 4N solution of hydrochloric-acid in ethyl acetate (4 ml) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue obtained was combined with aqueous sodium bicarbonate, extracted with dichloromethane, dried and concentrated to obtain 1-amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone as a colorless solid. A solution of the resultant 1-amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone and 1-(4-pyridyl)-4-piperidone (237 mg) in ethanol (30 ml) was dehydrated using a Soxlet extractor packed with molecular sieves 4A while refluxing for 24 hours. The reaction mixture was concentrated and 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 (265 mg) as colorless crystals.

Workup

  1. temperaturewhile refluxing for 24 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)
  4. customcrystallized from ether

Sources & evidence

ORD record
ord-e0df457e2a3f4533912f64690069f6dd
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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