Methyl iodide → HCID 13631918, compound

HRID 1905629Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:23][C:22](=[O:24])[C:9]3([CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:11][CH2:10]3)[N:8]=[C:7]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:6]=2[CH:31]=1.[H-].[Na+].[CH3:34]I>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:23]([CH3:34])[C:22](=[O:24])[C:9]3([CH2:10][CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:13][CH2:14]3)[N:8]=[C:7]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:6]=2[CH:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3.0 g (0.0069 mole) of 7-chloro-5-phenyl-1'-benzyl-spiro[1H-1,4-benzodiazepine-3,4'-piperidin]-2(3H)-one are dissolved in 25 ml of absolute dimethylformamide, and 0.3 g (0.007 mole) of sodium hydride (55-60% strength dispersion) is added at 20° C. After the mixture has been stirred for 20 minutes, it is cooled to 0° C., a solution of 1.0 g (0.0065 mole) of methyl iodide in 5 ml of absolute dimethylformamide is added dropwise and the mixture is stirred at 25° C. for 3 hours. The solvent is distilled off and the residue is purified by column chromatography over silica gel 60 (Merck). After the column has been eluted with methylene chloride/methanol (9:1), the oily base is obtained, which slowly crystallizes completely. Colorless crystals of melting point 169°-170° C.

Workup

stirringthe mixture is stirred at 25° C. for 3 hours
distillationThe solvent is distilled off
customthe residue is purified by column chromatography over silica gel 60 (Merck)
washAfter the column has been eluted with methylene chloride/methanol (9:1)
customthe oily base is obtained
customwhich slowly crystallizes completely

Sources & evidence

ORD record: ord-41a9553cc88a434aabacf98d0e8deb88
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04647560

Reaction notes

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