Hydrochloric Acid → 1-Amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

HRID 2086271Notes

Reaction equation

HRID 2086271 reaction equation
C(OC([NH:8][N:9]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:28])[CH:24]=3)[CH:19]=2)(=[O:17])=[O:16])[CH2:11][C:10]1=[O:29])=O)(C)(C)C.CO.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:8][N:9]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:28])[CH:24]=3)[CH:19]=2)(=[O:16])=[O:17])[CH2:11][C:10]1=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 227270351-(Tert-butoxycarbonylamino)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

Product 1

HCID 227270831-Amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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. concentrationThe reaction mixture was concentrated
  2. customthe residue obtained
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-550b6c9df9a94facb9fbeff0ebe20bbf
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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