4-methylpentan-1-amine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 10-[(2RS)-l-(l-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g) and 4-methylpentylamine hydrochloride (7.4 g) in absolute ethanol (30 cc) is saturated with hydrogen sulphide. The reaction mixture is then brought for 16 hours to a temperature in the region of 105° C. After being cooled, it is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter 3 cm) of silica gel (0.2-0.063 mm), eluting successively with methylene chloride (500 cc) and then with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol and collecting 30-cc fractions. Fractions 25 to 28 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) and there is added, with stirring, a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether followed by ethyl ether until a persistent cloudiness is formed. After 1 hour at a temperature in the region of 5° C., the solid formed is drained, washed with ethyl ether (3×10 cc) and dried under reduced pressure (5mm Hg; 0.7 kPa) at 40° C. N-(4-Methylpentyl)-l0-[(2RS)-l-(l-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride (1.7 g) is thereby obtained in the form of a yellow solid, m.p. 186° C. After being cooled it is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter 3 cm) of silica gel (0.2-0.063 mm) eluting successively with methylene chloride (500 cc) with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol and collecting 30-cc fractions concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) there is added is formed After 1 hour at a temperature in the region of 5° C. the solid formed washed with ethyl ether (3×10 cc) dried under reduced pressure (5mm Hg; 0.7 kPa) at 40° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 10-[(2RS)-l-(l-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g) and 4-methylpentylamine hydrochloride (7.4 g) in absolute ethanol (30 cc) is saturated with hydrogen sulphide. The reaction mixture is then brought for 16 hours to a temperature in the region of 105° C. After being cooled, it is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter 3 cm) of silica gel (0.2-0.063 mm), eluting successively with methylene chloride (500 cc) and then with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol and collecting 30-cc fractions. Fractions 25 to 28 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) and there is added, with stirring, a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether followed by ethyl ether until a persistent cloudiness is formed. After 1 hour at a temperature in the region of 5° C., the solid formed is drained, washed with ethyl ether (3×10 cc) and dried under reduced pressure (5mm Hg; 0.7 kPa) at 40° C. N-(4-Methylpentyl)-l0-[(2RS)-l-(l-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride (1.7 g) is thereby obtained in the form of a yellow solid, m.p. 186° C. After being cooled it is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter 3 cm) of silica gel (0.2-0.063 mm) eluting successively with methylene chloride (500 cc) with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol and collecting 30-cc fractions concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) there is added is formed After 1 hour at a temperature in the region of 5° C. the solid formed washed with ethyl ether (3×10 cc) dried under reduced pressure (5mm Hg; 0.7 kPa) at 40° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g) and 4-methylpentylamine hydrochloride (7.4 g) is absolute ethanol (30 cc) is saturated with hydrogen sulphide. The reaction mixture is then brought for 16 hours to a temperature in the region of 105° C. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica gel (0.2-0.063 mm), eluting successively with methylene chloride (500 cc) and then with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol, collecting 30-cc fractions. Fractions 25 to 28 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc), and a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether is added with stirring, followed by ethyl ether until a persistent cloudiness has formed. After 1 hour at a temperature in the region of 5° C., the solid formed is drained, washed with ethyl ether (3×10 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. N-(4-Methylpentyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride (1.7 g) is thereby obtained in the form of a yellow solid, m.p. 186° C. After cooling the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica gel (0.2-0.063 mm) eluting successively with methylene chloride (500 cc) with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol, collecting 30-cc fractions concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether is added has formed After 1 hour at a temperature in the region of 5° C. the solid formed washed with ethyl ether (3×10 cc) dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 10-[(2RS)-l-(l-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g) and 4-methylpentylamine hydrochloride (7.4 g) in absolute ethanol (30 cc) is saturated with hydrogen sulphide. The reaction mixture is then brought for 16 hours to a temperature in the region of 105° C. After being cooled, it is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter 3 cm) of silica gel (0.2-0.063 mm), eluting successively with methylene chloride (500 cc) and then with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol and collecting 30-cc fractions. Fractions 25 to 28 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) and there is added, with stirring, a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether followed by ethyl ether until a persistent cloudiness is formed. After 1 hour at a temperature in the region of 5° C., the solid formed is drained, washed with ethyl ether (3×10 cc) and dried under reduced pressure (5mm Hg; 0.7 kPa) at 40° C. N-(4-Methylpentyl)-l0-[(2RS)-l-(l-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride (1.7 g) is thereby obtained in the form of a yellow solid, m.p. 186° C. After being cooled it is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter 3 cm) of silica gel (0.2-0.063 mm) eluting successively with methylene chloride (500 cc) with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol and collecting 30-cc fractions concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) there is added is formed After 1 hour at a temperature in the region of 5° C. the solid formed washed with ethyl ether (3×10 cc) dried under reduced pressure (5mm Hg; 0.7 kPa) at 40° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2 g) and 4-methylpentylamine hydrochloride (7.4 g) is absolute ethanol (30 cc) is saturated with hydrogen sulphide. The reaction mixture is then brought for 16 hours to a temperature in the region of 105° C. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica gel (0.2-0.063 mm), eluting successively with methylene chloride (500 cc) and then with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol, collecting 30-cc fractions. Fractions 25 to 28 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc), and a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether is added with stirring, followed by ethyl ether until a persistent cloudiness has formed. After 1 hour at a temperature in the region of 5° C., the solid formed is drained, washed with ethyl ether (3×10 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. N-(4-Methylpentyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide hydrochloride (1.7 g) is thereby obtained in the form of a yellow solid, m.p. 186° C. After cooling the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The pasty residue (5 g) is purified by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica gel (0.2-0.063 mm) eluting successively with methylene chloride (500 cc) with a mixture (95:5 by volume) (500 cc) of methylene chloride and methanol, collecting 30-cc fractions concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C The residual orange oil (2.16 g) is dissolved in ethyl acetate (10 cc) a 3.3N solution (1.5 cc) of hydrochloric acid in isopropyl ether is added has formed After 1 hour at a temperature in the region of 5° C. the solid formed washed with ethyl ether (3×10 cc) dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C