Toluene → 6-Benzyl-1-oxa-6-azaspiro(2,5)octane

HRID 1410547Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:17]1(C)C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([O:14][CH2:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

18.9 g (0.1 mol) of 1-benzyl-4-piperidone, 24.2 g (0.11 mol) of trimethylsulfoxide iodide salt, 0.5 g of tetrabutyl ammonium bromide and 200 mL of toluene were added to a 500 mL round bottom flask, and slowly added dropwise at room temperature with 60 mL of (15%) sodium hydroxide solution. Then the reaction was heated to 80° C., reacted for 8 h, and then cooled to room temperature. The toluene layer was separated, and the water layer was extracted with toluene (50 mL×3). The toluene layer was combined, washed with water, saturated sodium chloride solution in sequence, dried with anhydrous sodium sulfate, and distilled under reduced pressure to recovery solvent to obtain light yellow oily liquid N-benzyl-1-oxa-6-azaspiro[2,5]-octane 19 g, yield: 93%. 1H-NMR (CDCl3, ppm) δ: 7.31-7.33 (5H, m), 3.56 (2H, s), 2.64 (2H, s), 2.53-2.62 (4H, m), 1.52-1.86 (4H, m).

Workup

customreacted for 8 h
temperaturecooled to room temperature
customThe toluene layer was separated
extractionthe water layer was extracted with toluene (50 mL×3)
washwashed with water, saturated sodium chloride solution in sequence
dry with materialdried with anhydrous sodium sulfate
distillationdistilled under reduced pressure to recovery solvent

Sources & evidence

ORD record: ord-45b94952089448bd8a6b42ecf6dfff06
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921563B2

Reaction notes

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