Ethanol → tert-Butyl 4-aminopiperidine-1-carboxylate--hydrogen chloride (1/1)

HRID 1893502Notes

Reaction equation

HRID 1893502 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.C(O)C.O.NN.[ClH:31].O1CCOCC1>C(OCC)C.C(OCC)(=O)C>[ClH:31].[NH2:3][CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 12063837tert-Butyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-1-carboxylateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 2756033tert-Butyl 4-aminopiperidine-1-carboxylate--hydrogen chloride (1/1)Yield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The compound (837 mg, 2.53 mmol) obtained in step B was added to ethanol (20 ml), hydrazine monohydrate (0.31 ml, 6.4 mmol) was added, and the mixture was heated under reflux for 1 hr. The reaction mixture was cooled, and diethyl ether was added to allow precipitation of a solid. The precipitated solid was filtered, and the obtained solution was concentrated under reduced pressure to give a colorless oil. The oil was dissolved in diethyl ether, 4N hydrochloric acid-dioxane solution (1 ml) was added at room temperature and the mixture was diluted with ethyl acetate to allow precipitation of a solid. This was filtered, washed with ethyl acetate, and dried under reduced pressure to give the title compound (598 mg, yield 100%) as a colorless solid.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hr
  4. temperatureThe reaction mixture was cooled
  5. customprecipitation of a solid
  6. filtrationThe precipitated solid was filtered
  7. concentrationthe obtained solution was concentrated under reduced pressure
  8. customto give a colorless oil
  9. customprecipitation of a solid
  10. filtrationThis was filtered
  11. washwashed with ethyl acetate
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-e595298cf72c46c884baaf0545286d16
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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