Hydrochloric Acid → Ethyl 1-benzyl-4-hydrazinylpiperidine-4-carboxylate hydrochloride

HRID 64305Notes

Reaction equation

HRID 64305 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([N:19](C(OC(C)(C)C)=O)[NH:20]C(OC(C)(C)C)=O)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:35]>CO>[ClH:35].[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([NH:19][NH2:20])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15663644Ethyl 1-benzyl-4-(N,N'-di-tert-butyloxycarbonylhydrazino)piperidin-4-ylcarboxylate

Product 1

HCID 117668154Ethyl 1-benzyl-4-hydrazinylpiperidine-4-carboxylate hydrochlorideYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of di-tert-butyl 1-(1-benzyl-4-(ethoxycarbonyl)piperidin-4-yl)hydrazine-1,2-dicarboxylate (1.0 g, 2.09 mmol) and con. HCl (1.0 mL) in MeOH (10 mL) was heated to reflux for 2 hr. The mixture was then concentrated to give the crude product (650 mg, 88.9%) as a yellow solid. MS (ESI, m/e) [M+1]+ 278.0.

Workup

  1. temperatureto reflux for 2 hr
  2. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-30db4601f7734b269e36785a41fea959
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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