Ethyl 1-benzyl-4-(N,N'-di-tert-butyloxycarbonylhydrazino)piperidin-4-ylcarboxylate → HCID 19610927, compound

HRID 1602326Notes

Reaction equation

HRID 1602326 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:30]([O:32][CH2:33][CH3:34])=[O:31])([N:14](C(OC(C)(C)C)=O)[NH:15]C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:35].CO>CO>[ClH:35].[ClH:35].[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([C:30]([O:32][CH2:33][CH3:34])=[O:31])([NH:14][NH2:15])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15663644Ethyl 1-benzyl-4-(N,N'-di-tert-butyloxycarbonylhydrazino)piperidin-4-ylcarboxylateHCID 21893726Hydrochloride methanol

Product 1

HCID 19610927HCID 19610927, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 1-benzyl-4-(N,N'-di-tert-butyloxycarbonylhydrazino)piperidin-4-yl-carboxylate (D26, 14.2 g, 0.030 mol) in methanol (50 ml) was treated with 10% HCl/methanol (100 ml) and heated under reflux for 2 h. The solution was concentrated in vacuo and the residue treated with dry toluene (80 ml) and again concentrated in vacuo to remove any traces of moisture. The residue was trituated with ether and the material filtered off and immediately placed in a vacuum dessicator to give the title compound (D27) (9.48 g, 90%) as a very hygroscopic orange solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. concentrationThe solution was concentrated in vacuo
  4. additionthe residue treated with dry toluene (80 ml)
  5. concentrationagain concentrated in vacuo
  6. customto remove any traces of moisture
  7. filtrationthe material filtered off

Sources & evidence

ORD record
ord-35fe8b9c976046188ce9411002df0134
Source dataset
uspto-grants-1999_11
Patent number
US05981545

Reaction notes

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