Hydrazinecarboxaldehyde → HCID 178451807, compound

HRID 1749663Notes

Reaction equation

C(O[C:4](=[NH:18])[CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)C.[CH:19]([NH:21][NH2:22])=O>O1CCOCC1>[NH:21]1[CH:19]=[N:18][C:4]([CH:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:9][CH2:10]2)=[N:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of tert-butyl 4-(ethoxy(imino)methyl)piperidine-1-carboxylate (51 g, 198.95 mmol) in dioxane (500 mL), was added formohydrazide (17.92 g, 298.43 mmol). This solution was left to stir at 40° C. overnight under N2 resulting in precipitation of a white solid (hydrazide intermediate). The reaction mixture was then heated to 80° C. for 6 h, cooled to room temperature and concentrated. The residue was dissolved in 500 mL of CH2Cl2 and 300 mL of water was added. The phases were decanted and the organic phase was washed with brine, dried over MgSO4, filtered and concentrated to afford tert-butyl 4-(1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate (46.0 g, 92%) as a white solid: 1H NMR Spectrum; (CDCl3) 1.47 (9H, s), 1.76 (2H, m), 1.98-2.11 (2H, m), 2.91 (2H, s), 2.97-3.08 (m, 1H), 4.06-4.23 (2H, m), 8.05 (1H, s); Mass Spectrum [M+H]+=no mass ion.

Workup

waitThis solution was left
temperaturecooled to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in 500 mL of CH2Cl2
addition300 mL of water was added
customThe phases were decanted
washthe organic phase was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-6352c42abc6e40058b994d138b08fe43
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156831B2

Reaction notes

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