Methyl iodide → 4-Benzyl-3-methoxymethyl-3-methylmorpholine

HRID 584230Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1([CH2:15][OH:16])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CI.[C:21](OCC)(=O)C>O1CCCC1.O>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1([CH2:15][O:16][CH3:21])[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 4-benzyl-3-hydroxymethyl-3-methylmorpholine (1 g) in tetrahydrofuran (10 ml) was added dropwise to a suspension of sodium hydride (60% oil suspension; 0.27 g) in tetrahydrofuran (20 ml) at room temperature under nitrogen atmosphere and the whole was stirred at 70° C. for 1 hour. After cooling, methyl iodide (0.34 ml) was added to the mixture and the whole was stirred at 40° C. for 1 hour. After cooling, ethyl acetate and water were added to the mixture and the organic layer was separated, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (1:4) as an eluent to give 4-benzyl-3-methoxymethyl-3-methylmorpholine (0.77 g) as an oil.

Workup

temperatureAfter cooling
stirringthe whole was stirred at 40° C. for 1 hour
temperatureAfter cooling
customthe organic layer was separated
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (1:4) as an eluent

Sources & evidence

ORD record: ord-40afcd7f042144a6833bddb00dee74cf
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924278B2

Reaction notes

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