Ether hydrochloride → 4-((Allyloxy)methyl)-4-methylpiperidine
Reaction equation
[CH2:1]([O:4][CH2:5][C:6]1([CH3:19])[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)[CH:2]=[CH2:3].Cl.CCOCC>>[CH2:1]([O:4][CH2:5][C:6]1([CH3:19])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1)[CH:2]=[CH2:3]Participants
3
Procedure
tert-Butyl 4-((allyloxy)methyl)-4-methylpiperidine-1-carboxylate (300 mg, 1.114 mmol) was placed in a 25 mL RBF. A 2N solution of HCl/ether was added (7 mL) and the vessel was sealed with a septa. The colorless homogeneous solution was stirred for 24 h. An aliquot was removed and analyzed by 1H NMR which indicated that the reaction was complete. The reaction mixture was concentrated in vacuo to give 221 mg (96%) of 4-((allyloxy)methyl)-4-methylpiperidine as a white sticky solid. 1H NMR (500 MHz, DMSO-d6) δ 8.88-8.42 (m, 2H), 5.90 (ddt, J=17.3, 10.5, 5.2 Hz, 1H), 5.35-5.12 (m, 2H), 3.96 (dt, J=5.2, 1.5 Hz, 2H), 3.24-3.16 (m, 2H), 3.12-2.93 (m, 4H), 1.70 (ddd, J=14.3, 10.0, 4.3 Hz, 2H), 1.43 (dt, J=14.2, 4.4 Hz, 2H), 0.98 (s, 3H).
Workup
- customthe vessel was sealed with a septa
- customAn aliquot was removed
- concentrationThe reaction mixture was concentrated in vacuo
Sources & evidence
- ORD record
- ord-4d8feb5366a749798edc89c6aa6db36c
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906929B2
Reaction notes
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