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

HRID 2209690Notes

Reaction equation

HRID 2209690 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-33f1d8233b754d6295d95d0a2c6ed9bf
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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