1,4-Dioxane hydrochloride → HCID 68312924, compound
Reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:14][CH2:13][CH2:12][N:11]2C(OC(C)(C)C)=O)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[ClH:22].O1CCOCC1>>[ClH:22].[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([CH:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]Participants
Procedure
To a mixture of tert-butyl 2-(piperidin-4-yl)pyrrolidine-1-carboxylate (400 mg, 1.57 mmol) in dry DMF (2.0 mL) at 0° C., was added NaH (132 mg, 3.30 mmol, 60% in mineral oil) in small portion. The reaction mixture was then warmed to room temperature with stirring for another 1 h. 2-iodopropane (2.0 mL) was added. The resulting mixture was stirred at room temperature for 24 h and then poured into the ice-water (20 mL). The resultant mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel chromatography eluting with a 5-10% gradient of MeOH in DCM to afford tert-butyl 2-(1-isopropylpiperidin-4-yl)pyrrolidine-1-carboxylate (302 mg, 65% yield). A solution of tert-butyl 2-(1-isopropylpiperidin-4-yl)pyrrolidine-1-carboxylate (302 mg, 1.02 mmol) in sat. HCl/dioxane (5 mL) was stirred at room temperature for 8 h. After removal of the solvent, 1-isopropyl-4-(pyrrolidin-2-yl)piperidine hydrochloride (232 mg, 100% yield) as yellow solid was obtained. LCMS (ESI) m/z: 197.2 [M+H+].
Workup
- customAfter removal of the solvent
Sources & evidence
- ORD record
- ord-ff133a858b0749acb167de7dcd4f33aa
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090628B2
Reaction notes
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