Methyl iodide → HCID 131723441, compound

HRID 2304571Notes

Reaction equation

[C:1]([CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]([C:17]#[N:18])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)#[N:2].[CH3:19][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI>O1CCCC1.C(OCC)C>[C:1]([CH:3]([CH3:19])[CH2:4][N:5]1[CH2:10][CH2:9][C:8]([C:17]#[N:18])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)#[N:2]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 1-(2-cyanoethyl)-4-cyano-4-phenyl-piperidine (2.81 g, 11.7 mmol) dissolved in tetrahydrofuran(110 mL) was cooled to −20° C. under an atmosphere of nitrogen and 1 M lithium bistrimethylsilylamide in tetrahydrofuran (12.3 ml) was added by syringe. The clear solution was allowed to stir for 30 min. and then methyl iodide (0.80 mL, 12.9 mmol) was added by syringe. This reaction mixture was stirred for 5 minutes and then warmed to room temperature and stirred for 30 minutes. The reaction was diluted with diethyl ether and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and the solvent removed to give an oil. This residue was purified by preparative centrifugal chromatography using a 5-50% ethyl acetate/hexane gradient to give the title compound which was used as is.

Workup

stirringThis reaction mixture was stirred for 5 minutes
temperaturewarmed to room temperature
stirringstirred for 30 minutes
washwashed with water and brine
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
customthe solvent removed
customto give an oil
customThis residue was purified by preparative centrifugal chromatography

Sources & evidence

ORD record: ord-a10625dfee214ed6b2a49138edf732ce
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436962B1

Reaction notes

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