Hydrochloric Acid → 1-[4-Bromo-2-(tert-butoxycarbonyl)benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

HRID 352731Notes

Reaction equation

HRID 352731 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.Cl.[Cl:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:25]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:27])=[O:26])[CH:19]=[CH:18]2.C(N([CH:40]([CH3:42])[CH3:41])CC)(C)C.Cl.Cl[CH2:45]Cl>>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:31]2[CH2:30][CH2:29][N:28]([S:25]([C:20]3[CH:19]=[CH:18][C:17]4[C:22](=[CH:23][CH:24]=[C:15]([Cl:14])[CH:16]=4)[CH:21]=3)(=[O:26])=[O:27])[CH2:33][CH2:32]2)=[O:7])=[C:4]([C:9]([O:8][C:40]([CH3:42])([CH3:45])[CH3:41])=[O:10])[CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 665904-Bromophthalic anhydrideHCID 81531DiisopropylethylamineHCID 227097661-(6-Chloronaphth-2-ylsulphonyl)piperazine hydrochloride

Product 1

HCID 227098641-[4-Bromo-2-(tert-butoxycarbonyl)benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

Procedure

In dichloromethane (200 ml), 4-bromophthalic anhydride (1.96 g) and 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride (3.00 g) were suspended under ice cooling. To the resulting suspension, diisopropylethylamine (3.76 ml) was added, followed by stirring for 20 minutes. To the reaction mixture, dilute hydrochloric acid and dichloromethane were added. The organic layer so separated was dried over anhydrous sodium sulfate. The solvent was concentrated so that the volume was reduced to 200 ml. To the concentrate, N,N′-diisopropyl-O-tert-butylisourea (2.6 g) was added under ice cooling and the resulting mixture was stirred at room temperature for 3 days. Dilute hydrochloric acid and dichloromethane were added to the reaction mixture. The organic layer so separated was dried over anhydrous sodium sulfate. The residue was purified by chromatography on a silica gel column (hexane : ethyl acetate=3:1˜1:1), whereby the title compound (1.78 g, 35%) was obtained as a colorless solid.

Workup

  1. customThe organic layer so separated
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated so that the volume
  4. additionTo the concentrate, N,N′-diisopropyl-O-tert-butylisourea (2.6 g) was added under ice cooling
  5. stirringthe resulting mixture was stirred at room temperature for 3 days
  6. additionDilute hydrochloric acid and dichloromethane were added to the reaction mixture
  7. customThe organic layer so separated
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customThe residue was purified by chromatography on a silica gel column (hexane : ethyl acetate=3:1˜1:1), whereby the title compound (1.78 g, 35%)
  10. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-fb717f7607894f03824b2627b0339b92
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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