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

HRID 1827188Notes

Reaction equation

HRID 1827188 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-1af9a44e758a4cd896ee01741b568a4c
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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