Methyl iodide → HCID 15096756, compound

HRID 2372764Notes

Reaction equation

[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11]([O:16][CH3:17])([O:14][CH3:15])[CH:10]([OH:18])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:21]I>CN(C)C=O>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11]([O:14][CH3:15])([O:16][CH3:17])[CH:10]([O:18][CH3:21])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-Phenylmethyl-3-hydroxy-4,4-dimethoxypiperidine (3b, 5.5g, 22 mmol) from Example 1 in 30ml of dimethylformamide was added slowly to a stirred suspension of sodium hydride (0.81g, 27 mmol, 80% oil suspension) in 100ml of dimethylformamide. The reaction mixture was warmed to 60° C. for 2 hours, then cooled to 0° C. whereupon methyl iodide (3.8g, 27 mmol) was slowly added to the mixture. The reaction mixture was stirred overnight at room temperature then quenched with 10ml of 10% sodium hydroxide solution. The reaction mixture was concentrated under vacuum, the residue slurried in 300ml of water and the aqueous mixture extracted with 3×100ml of ether. The combined organic layers were dried over magnesium sulfate, concentrated under vacuum, then purified by column chromatography (alumina; ethyl acetate/hexane; 2.5:1) to yield the intermediate 1-phenylmethyl-3-methoxy-4,4-dimethoxypiperidine (4b, 3.77g, 64.6%, Rf 0.63).

Workup

additionwas slowly added to the mixture
customthen quenched with 10ml of 10% sodium hydroxide solution
concentrationThe reaction mixture was concentrated under vacuum
extractionthe aqueous mixture extracted with 3×100ml of ether
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated under vacuum
custompurified by column chromatography (alumina; ethyl acetate/hexane; 2.5:1)

Sources & evidence

ORD record: ord-6fc36123d25840edbe7287ac4c58f4ca
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05100903

Reaction notes

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