Pyridine → 4-(4-Chlorophenyl)-3-pyrrolidin-N-yl-butan-2-one Oxime

HRID 133453Notes

Reaction equation

HRID 133453 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10](=O)[CH3:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl.[NH2:25][OH:26]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10](=[N:25][OH:26])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 222704894-(4-Chlorophenyl)-3-(1-pyrrolidinyl)-butan-2-one

Product 1

HCID 858679314-(4-Chlorophenyl)-3-pyrrolidin-N-yl-butan-2-one Oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-3-pyrrolidin-N-yl-butan-2-one (200 mg, 0.79 mmol, from Step B) dissolved in ethanol (2 mL), was added pyridine (63 mg, 0.79 mmol), and hydroxylamine hydrochloride (78 mg, 1.12 mmol). The mixture was refluxed for 24 h when LC/MS indicated disappearance of all starting material. The mixture was cooled to room temperature, concentrated under reduced pressure, treated with 33% aqueous potassium carbonated, and extracted with chloroform 5 times. The organic layers were combined and filtered over glass wool and dried over potassium carbonate. The filtrate obtained after passing through sintered glass was concentrated to give the oxime, homogeneous by TLC, Rf=0.3 in 95:5 CH2Cl2:MeOH. LC/MS m/e=267 (M+1). 500 MHz 1H NMR (CDCl3) δ 1.73 (m, 4H), 1.76 (s, 3H), 2.40 (m, 2H), 2.60 (m, 2H), 2.72 (dd, J=2.7, 10.8 Hz, 1H), 2.94 (dd, J=4.3,8.8 Hz, 1H), 3.03 (dd, J=4.4, 13.3 Hz, 1H), 3.8 (s, 1H), 6.96 (d, J=8.3 Hz, 2H), 7.11 (d, J=8.3 Hz, 2H)

Workup

  1. temperatureThe mixture was refluxed for 24 h when LC/MS
  2. concentrationconcentrated under reduced pressure
  3. additiontreated with 33% aqueous potassium
  4. extractionextracted with chloroform 5 times
  5. filtrationfiltered over glass wool
  6. dry with materialdried over potassium carbonate
  7. customThe filtrate obtained
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-341c454c5c1444aeae37959ab566f9c0
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Reaction notes

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