Hydrochloric Acid → 1-(1-Dimethylamino-2-propyl)-2-(4-bromophenyl)-1,4,6,7-tetrahydrothiopyrano[4,3-b]pyrrole hydrochloride

HRID 1730075Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=O)[CH2:7][CH:8]2[C:13](=O)[CH2:12][CH2:11][S:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:18][CH:19]([CH3:24])[CH2:20][N:21]([CH3:23])[CH3:22].[ClH:25]>Cl.C(O)C.CCOCC>[ClH:25].[CH3:22][N:21]([CH3:23])[CH2:20][CH:19]([N:18]1[C:6]([C:5]2[CH:16]=[CH:17][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:7][C:8]2[CH2:9][S:10][CH2:11][CH2:12][C:13]1=2)[CH3:24]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 5.5 g (0.017 mole) of 3-(4-bromophenacyl)-2,3,5,6-tetrahydrothiopyran-4-one [Example 2 (a)], 1.6 g of 2-amino-1-dimethylaminopropane, 16 ml. of ethanol, and one drop of concentrated hydrochloric acid is heated under reflux for 3 hours, cooled to 5°C, and filtered to provide a solid product. The resulting product is dissolved in ethanol, the solution is acidified with ethereal hydrogen chloride and diluted to the cloud point with ether. Upon standing, a solid separates. Recrystallization from ethanol gives off-white crystals of 1-(1-dimethylamino-2-propyl)-2-(4-bromophenyl)-1,4,6,7-tetrahydrothiopyrano[4,3-b]pyrrole hydrochloride, m.p. 237° to 238°C. dec.

Workup

temperatureunder reflux for 3 hours
filtrationfiltered
customto provide a solid product
customRecrystallization from ethanol

Sources & evidence

ORD record: ord-a2d5afde29434adca1a31cbb53aa3d1d
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03991076

Reaction notes

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