Ethanol → Ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate

HRID 1459459Notes

Reaction equation

C(O)C.Cl.[NH2:5][OH:6].[C:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1)#[N:8].C[O-].[Na+]>O>[NH2:8][C:7](=[N:5][OH:6])[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

Ethanol (150 ml) was added to a solution of hydroxylamine hydrochloride (17.25 g) in water (48 ml). Ethyl 4-cyano-1-piperidinecarboxylate (45 g) was added and the mixture was cooled. Sodium methoxide (44.4 g) was added dropwise at RT and the reaction mixture was stirred for 30 minutes at 60° C. The reaction mixture was cooled, filtered and the filtrate evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent evaporated, yielding 25 g (40%) of ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate. This fraction was redissolved in 2-propanone and converted into the hydrochloric acid salt (1:1) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 22 g (35%) of ethyl 4-[amino(hydroxyimino)methyl]-1-piperidine-carboxylate hydrochloride (intermediate 2).

Workup

temperaturethe mixture was cooled
temperatureThe reaction mixture was cooled
filtrationfiltered
customthe filtrate evaporated
customThe residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5)
customThe pure fractions were collected
customthe solvent evaporated

Sources & evidence

ORD record: ord-09199164904446ca90d349309dcc1eb3
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854261

Reaction notes

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