Pyridine → HCID 86634182, compound

HRID 1928854Notes

Reaction equation

HRID 1928854 reaction equation
[CH:1]([N:4]1[CH:9]2[CH2:10][CH2:11][CH2:12][CH:5]1[CH2:6][C:7](=O)[CH2:8]2)([CH3:3])[CH3:2].N1C=CC=CC=1.Cl.[NH2:21][OH:22]>C(O)C>[CH:1]([N:4]1[CH:9]2[CH2:10][CH2:11][CH2:12][CH:5]1[CH2:6][C:7](=[N:21][OH:22])[CH2:8]2)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 21677673HCID 21677673, compound

Product 1

HCID 86634182HCID 86634182, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 9-isopropyl-9-aza-bicyclo[3.3.1]nonan-3-one (CAS no: 56258-85-6) (5.0 g, 28 mmol) in ethanol (125 mL) and pyridine (3.3 mL, 41 mmol) with hydroxylamine hydrochloride (2.03 g, 29 mmol) was refluxed for 6 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 Na2SO4, filtered and the solvents evaporated to give the title compound as a white solid. (4.43 g, 82%); MS: m/e=197.1 (M+H−).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with diethyl ether leaving a solid, which
  3. customwas partitioned between dichloromethane and sodium carbonate solution
  4. dry with materialthe organic layers dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-405562a7eec04985a5aa1a324c7a48be
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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