Hydrogen chloride-ethyl acetate → 1-Tert-butyl-4-hydrazinylpiperidine hydrochloride

Reaction equation

[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][NH:12]C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[ClH:20].CCOC(C)=O>>[ClH:20].[C:1]([N:5]1[CH2:6][CH2:7][CH:8]([NH:11][NH2:12])[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetate

HCID 68313227Tert-butyl 2-(1-tert-butylpiperidin-4-yl)hydrazinecarboxylate

Product 1

HCID 683129781-Tert-butyl-4-hydrazinylpiperidine hydrochlorideYield 100%

Procedure

A mixture of tert-butyl 2-(1-tert-butylpiperidin-4-yl)hydrazinecarboxylate (350 mg, 1.29 mmol) in sat. HCl/EtOAc solution (20 mL) was stirred at room temperature overnight. The solvent was removed under reduce pressure to afford 1-tert-butyl-4-hydrazinylpiperidine hydrochloride (268 mg, 100% yield), which was used in the next step without further purification. LCMS (ESI) m/z: 172.3 [M+H+].

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-dd6454b4580c4cf09a1a3cb438a216e7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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