Hydroxyamine hydrochloride → 4-(1-Hydroxyimino-ethyl)-piperidine-1-carboxylic acid benzyl ester

HRID 1351551Notes

Reaction equation

HRID 1351551 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=O)[CH3:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[N:21][OH:22])[CH3:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19065050Benzyl 4-acetylpiperidine-1-carboxylate

Product 1

HCID 740642354-(1-Hydroxyimino-ethyl)-piperidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.0 g of 4-acetyl-piperidine-1-carboxylic acid benzyl ester, 25 mL of pyridine, and 6 g of hydroxylamine hydrochloride were heated to 100° C. for 12 h. The mixture was concentrated under reduced pressure and partitioned between 200 mL of ethyl acetate and 50 mL of 1N HCl. The organic extract was dried over magnesium sulfate and concentrated to dryness under reduced pressure. Drying under vacuum gave 4-(1-hydroxyimino-ethyl)-piperidine-1-carboxylic acid benzyl ester as a solid:

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompartitioned between 200 mL of ethyl acetate and 50 mL of 1N HCl
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customDrying under vacuum

Sources & evidence

ORD record
ord-29df7c429f6b49b98a222f702c749228
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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