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

HRID 2086281Notes

Reaction equation

HRID 2086281 reaction equation
C(OC(N1CCCCC1[CH2:14][NH:15][N:16]1[CH2:21][CH2:20][N:19]([S:22]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([Cl:35])[CH:31]=3)[CH:26]=2)(=[O:24])=[O:23])[CH2:18][C:17]1=[O:36])=O)(C)(C)C.CO.Cl.Cl.Cl[C:42]1[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=1>C(OCC)(=O)C.C(O)C.C(N(CC)CC)C>[Cl:35][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([S:22]([N:19]1[CH2:20][CH2:21][N:16]([N:15]([CH3:14])[CH:42]3[CH2:47][CH2:46][N:45]([C:42]4[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=4)[CH2:44][CH2:43]3)[C:17](=[O:36])[CH2:18]1)(=[O:23])=[O:24])[CH:34]=[CH:33]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 818524-Chloropyridine hydrochlorideHCID 695455571-{[1-(Tert-butoxycarbonyl)piperidinyl]methylamino}-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

Product 1

HCID 227271244-(6-Chloronaphthalene-2-sulfonyl)-1-{methyl[1-(4-pyridyl)-4-piperidinyl]amino}-2-piperazinoneYield 50.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-{[1-(tert-Butoxycarbonyl)piperidinyl]methylamino}-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (1.63 g) was combined with methanol (10 ml) and a 4N solution of hydrochloric acid in ethyl acetate (15 ml) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue obtained was combined with 4-chloropyridine hydrochloride (950 mg), triethylamine (3.8 g) and ethanol (100 ml), and reacted in a sealed tube at 150° C. for 15 hours. The reaction mixture was concentrated and the residue was combined with 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) and crystallized from ether to obtain the title compound (794 mg) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue obtained
  3. customreacted in a sealed tube at 150° C. for 15 hours
  4. concentrationThe reaction mixture was concentrated
  5. extractionextracted with dichloromethane
  6. customdried
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customwas purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)
  10. customcrystallized from ether

Sources & evidence

ORD record
ord-c4f6358cffc9463cb03f6480faa54e28
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

Loading…