Hydrochloric Acid → HCID 13631914, compound

HRID 1905630Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

0.6 g (0.0016 mole) of 7-chloro-5-phenyl-1'-methyl-spiro[1H-1,4-benzodiazepine-3,4'-piperidin]-2(3H)-one are dissolved in 15 ml of absolute dimethylformamide and reacted with 0.1 g of sodium hydride (55-60% strength dispersion) at 70° C. After 30 minutes, the mixture is cooled to 25° C., 0.22 g (0.0016 mole) of methyl iodide in 10 ml of absolute dimethylformamide is added and the mixture is stirred for 2 hours. After the solvent has been distilled off, the residue is taken up in water and the mixture is extracted with methylene chloride. For purification, the product is chromatographed on aluminum oxide 90 (Merck), activity level II-III, with a cyclohexane/methylene chloride/methanol mixture (6:3:1), and the base thus obtained is converted into the hydrochloride by treatment with diethyl ether/HCl.

Workup

distillationAfter the solvent has been distilled off
extractionthe mixture is extracted with methylene chloride
customFor purification
customthe product is chromatographed on aluminum oxide 90 (Merck), activity level II-III, with a cyclohexane/methylene chloride/methanol mixture (6:3:1)
customthe base thus obtained

Sources & evidence

ORD record: ord-87b9767b9a994855b9af3c0c3708d023
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04647560

Reaction notes

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