Methyl iodide → HCID 85612602, compound

HRID 1034286Notes

Reaction equation

[CH:1]1([N:7]([CH3:26])[C:8](=[O:25])[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>C1COCC1>[CH:1]1([N:7]([CH3:26])[C:8](=[O:25])[C:9]2[CH:10]=[CH:11][C:12]([CH:15]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH3:27])=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of N-cyclohexyl-N-methyl 4-(1H-benzimidazylmethyl)benzamide (347 mg, 1 mmol) in dry THF (20 ml) at -78 ° C. was added sodium bis(trimethylsilyl)amide (1.1 ml of 1M solution in THF) under argon. The mixture was left to stir at -78° C. for 40 minutes, a solution of methyl iodide (170 mg, 1.2 mmol) in dry THF (2 ml) was added and the mixture left to warm to ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and brine, the organic layer dried (Na2SO4), concentrated to give a crude product which was purified by column chromatography (flash silica gel, 4% methanol in DCM) to yield N-cyclohexyl-N-methyl 4-(1-(1H-benzimidazyl)ethyl)benzamide (40 mg, 11%) as a white crystalline solid.

Workup

waitThe mixture was left
waitthe mixture left
temperatureto warm to ambient temperature overnight
customThe reaction mixture was partitioned between ethyl acetate and brine
dry with materialthe organic layer dried (Na2SO4)
concentrationconcentrated
customto give a crude product which
customwas purified by column chromatography (flash silica gel, 4% methanol in DCM)

Sources & evidence

ORD record: ord-cf4e7b6967484aa4a995d8af425d4338
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05314880

Reaction notes

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