N-methyl-1-naphthalenemethylamine
1-chloro-6,6-dimethyl-hept-2-ene-4-yn
terbinafine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-methyl-1-naphthalenemethylamine; 1-chloro-6,6-dimethyl-hept-2-ene-4-yn With potassium carbonate In water at 80℃; for 4h; Large scale; Stage #2: With hydrogenchloride In water at 0 - 10℃; Large scale; | 93% |
N-(3-chloroallyl)-1-methyl-1-naphthylmethylamine
2,2-dimethyl-3-butyne
terbinafine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-(3-chloroallyl)-1-methyl-1-naphthylmethylamine; 3,3-Dimethylbut-1-yne With copper(l) iodide; N-butylamine; triphenylphosphine; palladium dichloride at 60 - 65℃; for 20h; Stage #2: With hydrogenchloride In water at 85 - 90℃; for 0.5h; Temperature; | 82.6% |
N-methyl-1-naphthalenemethylamine
3-hydroxy-6,6-dimethylhept-1-ene-4-yne
terbinafine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-6,6-dimethylhept-1-ene-4-yne With hydrogenchloride; trichlorophosphate In methanol at 0 - 20℃; for 20 - 24h; Stage #2: N-methyl-1-naphthalenemethylamine With sodium hydroxide at 80℃; Stage #3: With hydrogenchloride In dichloromethane; water at 20℃; | 81% |
terbinafin
terbinafine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water; butanone at 20 - 30℃; for 0.25h; | 75% |
With hydrogenchloride In water; butanone at 0 - 20℃; for 2.5h; Product distribution / selectivity; | 66.4% |
With hydrogenchloride In isopropyl alcohol at 0 - 20℃; for 0.5h; Product distribution / selectivity; | 63% |
1-(2'-furyl)-2,2-dimethylpropan-1-one tosyl hydrazone
N-methyl-1-naphthalenemethylamine hydrochloride
terbinafine hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide; sodium borohydrid In ethyl acetate; isopropyl alcohol; toluene | 50.3% |
With sodium hydroxide; sodium borohydrid In ethanol; ethyl acetate; toluene | 45.5% |
With sodium hydroxide; sodium borohydrid In ethyl acetate; toluene; tert-butyl alcohol | 19% |
1-(2'-furyl)-2,2-dimethylpropan-1-one benzenesulfonyl hydrazone
N-methyl-1-naphthalenemethylamine hydrochloride
terbinafine hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide; sodium borohydrid In ethyl acetate; isopropyl alcohol; toluene | 18.6% |
N-methyl-1-naphthalenemethylamine hydrochloride
terbinafine hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide; sodium borohydrid; acetic acid In ethyl acetate; toluene; tert-butyl alcohol | 17.4% |
1-(2'-furyl)-2,2-dimethylpropan-1-one 4-methoxybenzenesulfonyl hydrazone
N-methyl-1-naphthalenemethylamine hydrochloride
terbinafine hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide; sodium borohydrid In ethyl acetate; isopropyl alcohol; toluene | 11.7% |
1-(2'-furyl)-2,2-dimethylpropan-1-one methanesulfonyl hydrazone
N-methyl-1-naphthalenemethylamine hydrochloride
terbinafine hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide; sodium borohydrid In ethyl acetate; isopropyl alcohol; toluene | 10.9% |
1-(2'-furyl)-2,2-dimethylpropan-1-one tosyl hydrazone
N-methyl-1-naphthalenemethylamine hydrochloride
terbinafine hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide; sodium borohydrid In methanol; ethyl acetate; toluene | 10.4% |
N-methyl-1-naphthalenemethylamine hydrochloride
(Z)-1-chloro-6,6-dimethylhept-2-en-4-yne
1-chloro-6,6-dimethyl-hept-2-ene-4-yn
A
terbinafine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-methyl-1-naphthalenemethylamine hydrochloride; (Z)-1-chloro-6,6-dimethylhept-2-en-4-yne; 1-chloro-6,6-dimethyl-hept-2-ene-4-yn With sodium carbonate In water at 77 - 83℃; for 6 - 8h; Industry scale; Stage #2: With hydrogenchloride In water; toluene at 20 - 25℃; for 0.333333h; pH=0.5 - 1.5; Product distribution / selectivity; Industry scale; |
N-methyl-1-naphthalenemethylamine hydrochloride
1-chloro-6,6-dimethyl-hept-2-ene-4-yn
terbinafine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-methyl-1-naphthalenemethylamine hydrochloride; 1-chloro-6,6-dimethyl-hept-2-ene-4-yn With potassium carbonate In dimethyl sulfoxide at 25 - 60℃; for 4.25 - 6.5h; Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 10℃; for 0.5h; pH=1.5 - 2; Product distribution / selectivity; | |
Stage #1: N-methyl-1-naphthalenemethylamine hydrochloride; 1-chloro-6,6-dimethyl-hept-2-ene-4-yn; tetrabutylammomium bromide In water; toluene at 20 - 80℃; for 4 - 5h; Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 5℃; pH=1 - 2; Product distribution / selectivity; | |
Stage #1: N-methyl-1-naphthalenemethylamine hydrochloride; 1-chloro-6,6-dimethyl-hept-2-ene-4-yn With potassium carbonate; potassium iodide In ISOPROPYLAMIDE at 20 - 25℃; for 24h; Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 5℃; for 1h; pH=1.5 - 2; Product distribution / selectivity; |
(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)methylamine hydrochloride
1-Chloromethylnaphthalene
terbinafine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate In water; dimethyl sulfoxide; ethyl acetate |
1-chloro-6,6-dimethyl-2-hepten-4-yne
N-methyl-1-naphthalenemethylamine hydrochloride
terbinafine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-chloro-6,6-dimethyl-2-hepten-4-yne; N-methyl-1-naphthalenemethylamine hydrochloride With sodium carbonate In water; N,N-dimethyl-formamide at 11 - 60℃; for 6.25h; Stage #2: With hydrogenchloride In water for 0.5h; pH=0.2; | |
Stage #1: 1-chloro-6,6-dimethyl-2-hepten-4-yne; N-methyl-1-naphthalenemethylamine hydrochloride With sodium carbonate In water; N,N-dimethyl-formamide at 10 - 75℃; for 6.75h; Stage #2: With hydrogenchloride In dichloromethane; water at 10 - 15℃; for 0.5h; Product distribution / selectivity; | |
Stage #1: 1-chloro-6,6-dimethyl-2-hepten-4-yne; N-methyl-1-naphthalenemethylamine hydrochloride With sodium carbonate In water at 10 - 75℃; for 6.75h; Stage #2: With hydrogenchloride In dichloromethane; water at 10 - 15℃; for 0.5h; Product distribution / selectivity; |
1-chloro-6,6-dimethyl-2-hepten-4-yne
N-methyl-1-naphthalenemethylamine
terbinafine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-chloro-6,6-dimethyl-2-hepten-4-yne; N-methyl-1-naphthalenemethylamine With sodium hydroxide In water at 20 - 100℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃; for 1h; |
1. Introduction of Terbinafine hydrochloride
Terbinafine hydrochloride, with the IUPAC Name of (E)-N,6,6-Trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride, has the Classification Code which include Antifungal; Drug / Therapeutic Agent; Human Data; Reproductive Effect. And this chemical belongs to the Product Categories which include Antifungal; APIs; Acetylenes; Antifungals for Research and Experimental Use; Biochemistry; Functionalized Acetylenes; Amines; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals; Terbinafine.
.
2. Properties of Terbinafine hydrochloride
Terbinafine hydrochloride has the following properties: (1)H bond acceptors: 1; (2)Freely Rotating Bonds: 5; (3)Polar Surface Area: 3.24; (4)Flash Point: 183.7 °C; (5)Enthalpy of Vaporization: 67.13 kJ/mol; (6)Boiling Point: 417.9 °C at 760 mmHg; (7)Vapour Pressure: 3.42E-07 mmHg at 25°C.
3. Toxicity of Terbinafine hydrochloride
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | subcutaneous | > 2gm/kg (2000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: ATAXIA BLOOD: CHANGES IN SPLEEN | Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7888, 1990. |
rat | LD50 | skin | > 2gm/kg (2000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: ATAXIA BLOOD: CHANGES IN SPLEEN | Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7922, 1990. |
rat | LD50 | subcutaneous | > 2gm/kg (2000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BLOOD: CHANGES IN SPLEEN BEHAVIORAL: ATAXIA | Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7922, 1990. |
women | TDLo | oral | 210mg/kg/6W-I (210mg/kg) | SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE | Lancet. Vol. 339, Pg. 1483, 1992. |
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