1-(t-Butoxycarbonyl)4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine → 4-(1-(6-Chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine

HRID 2288730Notes

Reaction equation

HRID 2288730 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[C:30]([Cl:35])[CH:31]=4)[CH:26]=3)(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[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[CH2:18][CH2:17][N:16]([C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[O:15])[CH2:21][CH2:20]1)(=[O:23])=[O:24])[CH:34]=[CH:33]2

Participants

3

Reactant 1

HCID 121120201-(t-Butoxycarbonyl)4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine

Product 1

HCID 121120194-(1-(6-Chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidineYield 89.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(t-Butoxycarbonyl)4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine (28 g) was added in portions with stirring to trifluoroacetic acid (100 ml). The mixture was stirred for one hour. The trifluoroacetic acid was removed by evaporation. Aqueous 2M sodium hydroxide solution (150 ml) was added to the residue and the mixture extracted with dichloromethane (500 ml). The dichloromethane extract was washed with aqueous 2M sodium hydroxide solution (2×50 ml), water (2×100 ml), dried (MgSO4) and evaporated to give a solid which was recrystallised from a mixture of ethyl acetate/hexane to give 4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine (20.31 g);

Workup

  1. customThe trifluoroacetic acid was removed by evaporation
  2. additionAqueous 2M sodium hydroxide solution (150 ml) was added to the residue
  3. extractionthe mixture extracted with dichloromethane (500 ml)
  4. extractionThe dichloromethane extract
  5. washwas washed with aqueous 2M sodium hydroxide solution (2×50 ml), water (2×100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a solid which
  9. customwas recrystallised from a mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-05f784ed45764dd5ab89f3bd270d2374
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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