Ethanol → 4-[N-hydroxy-carbamoyl]-4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-piperidine

HRID 264305Notes

Reaction equation

HRID 264305 reaction equation
C([O:5][NH:6][C:7]([C:9]1([N:22]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:8])(C)(C)C.C(O)C>ClC(Cl)C>[OH:5][NH:6][C:7]([C:9]1([N:22]([S:30]([C:33]2[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=2)(=[O:32])=[O:31])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][CH2:10]1)=[O:8]

Participants

4

Reactant 2

HCID 702EthanolHCID 229070474-[N-t-Butyloxycarbamoyl]-4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]piperidine

Product 1

HCID 152966014-[N-hydroxy-carbamoyl]-4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-piperidine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

4-[N-t-Butyloxycarbamoyl]-4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]piperidine is dissolved in dichloroethane (60 mL) and ethanol (1.0 mL) in a glass sealed tube. Hydrochloric acid gas (from a lecture bottle) is bubbled through the solution for 30 minutes at -10° C. The tube is sealed, gradually warmed to room temperature, and stirred overnight. At this point, hydrochloric acid gas is again bubbled through the reaction mixture as done previously and stirred at room temperature for an additional 24 hours. The reaction mixture is reduced to 1/3 volume in vacuo and triturated with diethyl ether. The solid is filtered off and dried in vacuo to provide 4-[N-hydroxy-carbamoyl]-4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-piperidine, m.p. 135.5°-142° C.

Workup

  1. customHydrochloric acid gas (from a lecture bottle) is bubbled through the solution for 30 minutes at -10° C
  2. customThe tube is sealed
  3. customAt this point, hydrochloric acid gas is again bubbled through the reaction mixture
  4. stirringstirred at room temperature for an additional 24 hours
  5. customtriturated with diethyl ether
  6. filtrationThe solid is filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-cc1249f2ab984b49ac92208a5183b969
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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