Triethylamine → 1-(1-Acetoimidoyl-4-piperidinylamino)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone Hydrochloride

HRID 2086277Notes

Reaction equation

HRID 2086277 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([NH:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:18](=[O:29])[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[CH2:30]([N:32](CC)CC)[CH3:31].C(=N)(OCC)C>CO>[ClH:2].[C:30]([N:26]1[CH2:25][CH2:24][CH:23]([NH:22][N:19]2[CH2:20][CH2:21][N:16]([S:13]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([Cl:2])[CH:4]=4)[CH:9]=3)(=[O:14])=[O:15])[CH2:17][C:18]2=[O:29])[CH2:28][CH2:27]1)(=[NH:32])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65066Ethyl acetimidateHCID 227272664-(6-Chloronaphthalene-2-sulfonyl)-1-(4-piperidinylamino)-2-piperazinone hydrochloride

Product 1

HCID 227272121-(1-Acetoimidoyl-4-piperidinylamino)-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(tert-Butoxycarbonyl)-4-piperidinylamino]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (300 mg) was combined with a 4N solution of hydrochloric acid in ethyl acetate (10 ml) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated to obtain a crude crystal of 4-(6-chloronaphthalene-2-sulfonyl)-1-(4-piperidinylamino)-2-piperazinone hydrochloride. A solution of the resultant 4-(6-chloronaphthalene-2-sulfonyl)-1-(4-piperidinylamino)-2-piperazinone hydrochloride and triethylamine (1.16 g) in methanol (15 ml) was combined with ethyl acetoimidate (712 mg) and stirred at room temperature for 15 hours. The reaction mixture was concentrated and the residue was dissolved in dichloromethane, washed with a 1N aqueous solution of sodium hydroxide, dried and concentrated. The resultant residue was dissolved in ethyl acetate, combined with a solution of hydrochloric acid in ethyl acetate to precipitate a hydrochloride, which was collected by filtration and dried to obtain the title compound (243 mg) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with a 1N aqueous solution of sodium hydroxide
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe resultant residue was dissolved in ethyl acetate
  7. customto precipitate a hydrochloride, which
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-ecd6500b46fa4beeaa5418c87679d15a
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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