Hydrochloric Acid → (R)-1-(2-((amino)oxy)ethyl)-3-piperidinecarboxylic acid dihydrochloride
Reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][N:15]2C(=O)C3=CC=CC=C3C2=O)[CH2:7]1)=[O:5])C.[ClH:26]>C(O)(=O)C>[ClH:26].[ClH:26].[NH2:15][O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1Participants
4
Conditions
- Temperature
- 80 °C
Procedure
A mixture of the above ester (3.3 g, 10 mmol), acetic acid (7 ml) and concentrated hydrochloric acid (4.2 ml) was heated at 80° C. for 1.5 h. The reaction mixture was cooled to 5° C., filtered and the filterpad washed with cold acetic acid (2×2 ml). The solvent was evaporated from the filtrate in vacuo and the residue was dissolved in warm absolute ethanol (10 ml) and left for crystallisation. The precipitate was collected and dried in vacuo to give 1.1 g of (R)-1-(2-((amino)oxy)ethyl)-3-piperidinecarboxylic acid dihydrochloride.
Workup
- temperatureThe reaction mixture was cooled to 5° C.
- filtrationfiltered
- washthe filterpad washed with cold acetic acid (2×2 ml)
- customThe solvent was evaporated from the filtrate in vacuo
- dissolutionthe residue was dissolved in warm absolute ethanol (10 ml)
- waitleft for crystallisation
- customThe precipitate was collected
- customdried in vacuo
Sources & evidence
- ORD record
- ord-9091f33951ef47858d07e68ec2861708
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05608069
Reaction notes
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