Pyridine → HCID 86634183, compound

HRID 1695637Notes

Reaction equation

HRID 1695637 reaction equation
[CH:1]([N:4]1[CH:9]2[CH2:10][CH2:11][CH:5]1[CH2:6][C:7](=O)[CH2:8]2)([CH3:3])[CH3:2].N1C=CC=CC=1.Cl.[NH2:20][OH:21]>C(O)C>[CH:1]([N:4]1[CH:9]2[CH2:10][CH2:11][CH:5]1[CH2:6][C:7](=[N:20][OH:21])[CH2:8]2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1030098-(Propan-2-yl)-8-azabicyclo[3.2.1]octan-3-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 86634183HCID 86634183, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 8-isopropyl-8-aza-bicyclo[3.2.1]octan-3-one (CAS 3423-28-7)(20.0 g, 120 mmol) in ethanol (500 ml) and pyridine (14.5 ml, 179 mmol) with hydroxylamine hydrochloride (8.81 g, 127 mmol) was refluxed for 16 h. Cooled to 23° C., the precipitate was filtered off, washed with diethyl ether leaving a solid, which was partitioned between dichloromethane and sodium carbonate solution, the organic layers dried over sodium sulfate, filtered and the solvents evaporated to give the title compound as a white solid. (17.7 g, 82%), MS: m/e=183.2 (M+H+).

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationthe precipitate was filtered off
  3. washwashed with diethyl ether leaving a solid, which
  4. customwas partitioned between dichloromethane and sodium carbonate solution
  5. dry with materialthe organic layers dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents evaporated

Sources & evidence

ORD record
ord-46661e8df7d146f0b2f383a281980a0e
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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