Diethyl Ether → n-Hydroxy-1-[4-(4-chlorophenyl)-piperazine-1-sulfonyl]-piperidine-2-(rs)-carboxamide

HRID 609684Notes

Reaction equation

HRID 609684 reaction equation
FC(F)(F)C(O)=O.[O:8]([NH:16][C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]1[S:25]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)(=[O:27])=[O:26])=[O:18])[Si](C(C)(C)C)(C)C.C(OCC)C>C(Cl)Cl>[OH:8][NH:16][C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]1[S:25]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=2)[CH2:30][CH2:29]1)(=[O:26])=[O:27])=[O:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 22615606n-Tert-butyldimethylsiloxy-1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]piperidine-2-(rs)-carboxamide

Product 1

HCID 10341094n-Hydroxy-1-[4-(4-chlorophenyl)-piperazine-1-sulfonyl]-piperidine-2-(rs)-carboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (few drops) was added to a solution of N-tert-butyldimethylsiloxy-1-[4-(4-chlorophenyl)piperazine-1-sulfonyl]pipeidine-2-(RS)-carboxamide (63 mg, 0.12 mmol), [prepared as described in Step 2 above], in methylene chloride (2 ml) and the reaction mixture was stirred at RT for 45 min. The organics were removed in vacuo and the residue was dissolved in methylene chloride (25 ml) and the washed with sat. sodium bicarbonate, brine, and dried over MgSO4. The solvent was removed in vacuo to give a foam which was redissolved in a minimum amount of methylene chloride. Diethyl ether was added and the resulting white precipitates were filtered to give N-hydroxy-1-[4-(4-chlorophenyl)-piperazine-1-sulfonyl]-piperidine-2-(RS)-carboxamide (67%).

Workup

  1. customThe organics were removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride (25 ml)
  3. washthe washed with sat. sodium bicarbonate, brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customto give a foam which
  7. customthe resulting white precipitates
  8. filtrationwere filtered

Sources & evidence

ORD record
ord-0e7d7b255f104cd4baea464201f5f657
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

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