1-Propanamine, 3-chloro-N,N,2-trimethyl-, hydrochloride (1:1)

white to off-white powder

General procedure: A mixture of 6H-9-fluoroquinobenzothiazine (1) (134mg, 0.5mmol) sodium hydroxide (300mg, 7.5mmol) and hydrochloride of dialkylaminoalkyl chloride (1.5mmol, 2-diethylaminoethyl ' 260mg, 3-dimethylaminopropyl ' 240mg, 3-dimethylamino-2-methylpropyl ' 260mg, 2-(1-pyrrolidyl)ethyl ' 260mg, 2-(1-piperidyl)ethyl ' 280mg, 2-(1-methyl-2-piperydinyl)ethyl ' 300mg) in dry dioxane (5mL) was refluxed for 3h. After cooling the reaction mixture was poured into water (25mL) and extracted with chloroform (3×10mL). The combined extracts were washed with water to pH=7 and dried over Na2SO4. Chloroform was evaporated and the residue was purified by column chromatography (Al2O3, CHCl3) to give compounds 5'10:General procedure: A mixture of 6H-quinobenzothiazine 3a (0.13 g, 0.5 mmol) [or 9-chloro-6H-quinobenzothiazine 3c (0.14 g, 0.5 mmol) or 9-methylthio-6H-quinobenzothiazine 3f (0.15 g, 0.5 mmol)], sodium hydroxide (0.30 g, 7.5 mmol) and hydrochloride of dialkylaminoalkylchloride (1.5 mmol, 2-diethylaminoethyl - 0.26 g, 3-dimethylaminopropyl - 0.24 g, 3-dimethylamino-2-methylpropyl - 0.26 g, 2-(1-pyrrolidyl)ethyl - 0.26 g, 2-(1-piperidyl)ethyl - 0.28 g, 2-(1-methyl-2-piperydinyl)ethyl - 0.30 g) in dry dioxane (5 mL) was refluxed for 3 h. After cooling the reaction mixture was poured into water (25 mL) and extracted with chloroform (3 x 10 mL). The combined extracts were washed with water to pH = 7 and dried over Na2SO4. Chloroform was evaporated in vacuo and the residue was purified by column chromatography (Al2O3, CHCl3) to give compounds 6-11.General procedure: A mixture of 6H-quinobenzothiazine 3a (0.13 g, 0.5 mmol) [or 9-chloro-6H-quinobenzothiazine 3c (0.14 g, 0.5 mmol) or 9-methylthio-6H-quinobenzothiazine 3f (0.15 g, 0.5 mmol)], sodium hydroxide (0.30 g, 7.5 mmol) and hydrochloride of dialkylaminoalkylchloride (1.5 mmol, 2-diethylaminoethyl - 0.26 g, 3-dimethylaminopropyl - 0.24 g, 3-dimethylamino-2-methylpropyl - 0.26 g, 2-(1-pyrrolidyl)ethyl - 0.26 g, 2-(1-piperidyl)ethyl - 0.28 g, 2-(1-methyl-2-piperydinyl)ethyl - 0.30 g) in dry dioxane (5 mL) was refluxed for 3 h. After cooling the reaction mixture was poured into water (25 mL) and extracted with chloroform (3 x 10 mL). The combined extracts were washed with water to pH = 7 and dried over Na2SO4. Chloroform was evaporated in vacuo and the residue was purified by column chromatography (Al2O3, CHCl3) to give compounds 6-11.General procedure: A mixture of 6H-quinobenzothiazine 3a (0.13 g, 0.5 mmol) [or 9-chloro-6H-quinobenzothiazine 3c (0.14 g, 0.5 mmol) or 9-methylthio-6H-quinobenzothiazine 3f (0.15 g, 0.5 mmol)], sodium hydroxide (0.30 g, 7.5 mmol) and hydrochloride of dialkylaminoalkylchloride (1.5 mmol, 2-diethylaminoethyl - 0.26 g, 3-dimethylaminopropyl - 0.24 g, 3-dimethylamino-2-methylpropyl - 0.26 g, 2-(1-pyrrolidyl)ethyl - 0.26 g, 2-(1-piperidyl)ethyl - 0.28 g, 2-(1-methyl-2-piperydinyl)ethyl - 0.30 g) in dry dioxane (5 mL) was refluxed for 3 h. After cooling the reaction mixture was poured into water (25 mL) and extracted with chloroform (3 x 10 mL). The combined extracts were washed with water to pH = 7 and dried over Na2SO4. Chloroform was evaporated in vacuo and the residue was purified by column chromatography (Al2O3, CHCl3) to give compounds 6-11.

Cyamemazine intermediate.

Molecular Weight:172.09
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:171.0581549
Monoisotopic Mass:171.0581549
Topological Polar Surface Area:3.2
Heavy Atom Count:9
Complexity:54.5
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes