Hydrochloric Acid → (+)-4,5,6,7-Tetrahydro-6-[2-[4-(2-pyridinyl)-1-piperazinyl]ethyl]-2-benzothiazolamine
Reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].II.[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]2)[CH2:15][CH2:14]1.Cl>>[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][C:24]3[N:1]=[C:2]([NH2:4])[S:3][C:23]=3[CH2:22]2)[CH2:17][CH2:18]1Participants
Conditions
- Temperature
- 150 °C
Procedure
Thiourea (7.56 g) and iodine (12.61 g) are mixed and stirred mechanically under a stream of nitrogen. To this mixture is added 4-[2-[4-(2-pyridinyl)-1-piperazinyl]ethyl]cyclohexanone (9.52 g) (Example J) and the temperature gradually increased to 150° C. Following 30 minutes at this temperature, the mixture is cooled to room temperature and treated with 250 ml of a 10% solution of hydrochloric acid. Some insoluble material is filtered, the filtrate made basic with ammonium hydroxide, and extracted with chloroform (2×500 ml). The combined organic extracts are dried over magnesium sulfate and concentrated. The crude reaction mixture is purified by MPLC (silica; 5% methanol, 95% chloroform) to give the title compound as a light yellow solid; mp 194°-197° C.
Workup
- temperaturethe mixture is cooled to room temperature
- filtrationSome insoluble material is filtered
- extractionextracted with chloroform (2×500 ml)
- dry with materialThe combined organic extracts are dried over magnesium sulfate
- concentrationconcentrated
- customThe crude reaction mixture
- customis purified by MPLC (silica; 5% methanol, 95% chloroform)
Sources & evidence
- ORD record
- ord-80651280567a48999bdfd9bf0ca98d00
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04988699
Reaction notes
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