Sodium Hydroxide → HCID 9867305, compound

HRID 2226113Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[CH:23]=[C:24]([O:29][CH3:30])[C:25]([O:27][CH3:28])=[CH:26][C:21]=3[C@H:20]3[C@H:15]([CH2:16][CH2:17][N:18]([CH3:31])[CH2:19]3)[N:14]=2)=[CH:9][CH:8]=1.[OH-].[Na+]>O1CCOCC1.N1C=CC=CC=1>[CH3:30][O:29][C:24]1[C:25]([O:27][CH3:28])=[CH:26][C:21]2[C@H:20]3[C@H:15]([CH2:16][CH2:17][N:18]([CH3:31])[CH2:19]3)[N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=3)[C:22]=2[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 0.6 ml methanesulphonyl chloride in 3 ml absolute dioxane is added dropwise to a solution of 2.1 g rac-cis-6-(4-aminophenyl)-8,9-dimethoxy-1,2,3,4,4a, 10b-hexahydro-2-methyl-benzo[c ][1,6]naphthyridine in 20 ml absolute pyridine, and the mixture is then stirred at 60° C. for a further 3 h. After cooling, the mixture is poured onto 100 ml of an ice/water mixture, rendered alkaline with dilute sodium hydroxide solution and extracted with n-butanol. After the n-butanol has been evaporated off, the residue which remains is extracted with methylene chloride and the organic phase is dried over sodium sulphate and then concentrated. 2.4 g of the title compound are obtained as the residue and are converted into the dihydrochloride with ethereal HCl, and the product is recrystallized from non-dried methanol. Yield: 2.3 g of the title compound as the dihydrochloride hydrate. M.p. 239°-240° C. (decomposition).

Workup

temperatureAfter cooling
extractionextracted with n-butanol
customAfter the n-butanol has been evaporated off
extractionthe residue which remains is extracted with methylene chloride
dry with materialthe organic phase is dried over sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-be0c0c4e80dd42fc8863e4aa3dd0e8e4
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05346904

Reaction notes

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