Hydrochloric Acid → (3S)-3-methyl-4-((2R)-2-piperazinylmethyl)morpholine trihydrochloride
Reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[CH2:8][C@H:9]1[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11][N:10]1C(OC(C)(C)C)=O.[ClH:29]>CCOC(C)=O>[ClH:29].[ClH:29].[ClH:29].[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[CH2:8][C@H:9]1[CH2:14][NH:13][CH2:12][CH2:11][NH:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A 250-mL round-bottomed flask was charged with di-tert-butyl (2S)-2-(((3S)-3-methyl-4-morpholinyl)methyl)-1,4-piperazinedicarboxylate (2.46 g, 6.16 mmol, step 2), HCl (4.0 M solution in 1,4-dioxane, 4.62 mL, 18.5 mmol, Sigma-Aldrich, St. Louis, Mo.) and EtOAc (100 mL). The reaction mixture was heated at 70° C. for 3 h. At this time, additional HCl (4.0 M solution in 1,4-dioxane, 5.00 mL, 20.0 mmol) was added and heating at 70° C. was resumed for an additional 3 h. The reaction mixture was cooled to room temperature and the resulting white solid was collected, washed with EtOAc and dried overnight under reduced pressure to afford (3S)-3-methyl-4-((2R)-2-piperazinylmethyl)morpholine trihydrochloride (2.05 g) as a white powder.
Workup
- temperatureheating at 70° C.
- temperatureThe reaction mixture was cooled to room temperature
- customthe resulting white solid was collected
- washwashed with EtOAc
- customdried overnight under reduced pressure
Sources & evidence
- ORD record
- ord-699f67b155dd4dd09fed7cc07db7616d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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