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

HRID 1459459노트

반응식

HRID 1459459 반응식
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

참가 물질

6

반응물 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 4060541Ethyl 4-cyanopiperidine-1-carboxylateHCID 10942334Sodium Methoxide

생성물 1

HCID 54150879Ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate수율 47%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-09199164904446ca90d349309dcc1eb3
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05854261

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