Hydroxyamine hydrochloride → HCID 86761959, compound

HRID 453898Notes

Reaction equation

HRID 453898 reaction equation
[N:1]1([C:5]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].Cl.[NH2:24][OH:25]>CO.O>[N:1]1([C:5]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:10][CH2:9][C:8](=[N:24][OH:25])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium Bicarbonate2×HCID 57475117HCID 57475117, compound

Product 1

HCID 86761959HCID 86761959, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-(azetidin-1-yl)-4-phenylcyclohexanone (8.4 g) in methanol (84 ml), water (84 ml) and sodium hydrogen carbonate (10.08 g) was stirred for 5 min at room temperature, then hydroxylamine hydrochloride (6.95 g) was added in portions and the mixture was stirred for 8 hours at RT. A further 0.4 equiv. of sodium hydrogen carbonate and hydroxylamine hydrochloride were then added, and stirring was carried out for 16 h at room temperature. Then the reaction mixture was concentrated under reduced pressure, the organic phase was separated off and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure to yield the desired crude product. Yield: 6 g (67% crude)

Workup

  1. stirringstirring
  2. waitwas carried out for 16 h at room temperature
  3. concentrationThen the reaction mixture was concentrated under reduced pressure
  4. customthe organic phase was separated off
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0b018f88ec24c38b9e869a28113df87
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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