CAS No.67165-56-4,Diclofensine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	67165-56-4
Name:	Diclofensine
Article Data:	5

Formula:	C₁₇H₁₇Cl₂NO
Molecular Weight:	322.234
Synonyms:	Ro 8-4650;Diclofensine;4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-7-methoxy-2-methylisoquinoline;
Density:	1.242 g/cm³
Boiling Point:	422.595 °C at 760 mmHg
Flash Point:	209.378 °C
PSA:	12.47000
LogP:	4.51720

Synthetic route

: 802051-24-7
1-(3,4-dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanol

A: 692248-97-8
4-(3,4-dichlorophenyl)-5-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

B: 67165-56-4
Diclofensine

Conditions

Conditions	Yield
Stage #1: 1-(3,4-dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanol With sulfuric acid In dichloromethane at 0℃; for 28h; Stage #2: With sodium hydroxide In dichloromethane pH=9;	A 10% B 59%
Stage #1: 1-(3,4-dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanol With sulfuric acid In dichloromethane at 0℃; for 28h; Stage #2: With sodium hydroxide In dichloromethane pH=~ 9;
Stage #1: 1-(3,4-dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanol With sulfuric acid In dichloromethane; water at 0℃; for 28h; Stage #2: With sodium hydroxide In dichloromethane; water pH=~ 9;

: 1254941-88-2
1-(3,4-dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanone

: 67165-56-4
Diclofensine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / methanol / 2 h / 0 °C 2.1: sulfuric acid / dichloromethane; water / 28 h / 0 °C 2.2: pH ~ 9 View Scheme

: 41789-95-1
1-(3-methoxyphenyl)-N-methylmethanamine

: 67165-56-4
Diclofensine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dichloromethane / 1 h / 0 °C 1.2: 1 h / 0 °C 2.1: sodium tetrahydroborate / methanol / 2 h / 0 °C 3.1: sulfuric acid / dichloromethane; water / 28 h / 0 °C 3.2: pH ~ 9 View Scheme

: 591-31-1
3-methoxy-benzaldehyde

: 67165-56-4
Diclofensine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate / methanol; water / 2 h / 0 °C 2.1: dichloromethane / 1 h / 0 °C 2.2: 1 h / 0 °C 3.1: sodium tetrahydroborate / methanol / 2 h / 0 °C 4.1: sulfuric acid / dichloromethane; water / 28 h / 0 °C 4.2: pH ~ 9 View Scheme

: 67165-56-4
Diclofensine

: (+)-4-(3,4-dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

: (-)-4-(3,4-dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
With CHIRALPAK AD Purification / work up; Resolution of racemate;
With Chiralpak AD column In diethylamine; isopropyl alcohol Purification / work up; Resolution of racemate;

: 50893-53-3
carbonochloridic acid 1-chloro-ethyl ester

: 67165-56-4
Diclofensine

: C19H18Cl3NO3

Conditions

Conditions	Yield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In 1,2-dichloro-ethane Reflux;

: 67165-56-4
Diclofensine

A: 50560-45-7
(-)-4-(3,4-dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

B: 50560-38-8
(S)-diclofensine

Conditions

Conditions	Yield
With Chiralpak AD column In n-heptane; diethylamine; isopropyl alcohol Purification / work up; Resolution of racemate;

: 67165-56-4
Diclofensine

: 1255925-44-0
4-(3,4-dichlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl trifluoromethanesulfonate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate 2: hydrogen bromide / water; acetic acid / 8 h / Reflux 3: pyridine / dichloromethane / 1 h / -78 - 0 °C View Scheme

: 67165-56-4
Diclofensine

: 1254941-99-5
7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate 2: hydrogen bromide / water; acetic acid / 8 h / Reflux 3: pyridine / dichloromethane / 1 h / -78 - 0 °C 4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere 5: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 1 h / 80 °C / Inert atmosphere 6: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 1,2-dichloro-ethane / 19.33 h / 0 - 20 °C 7: methanol / 1 h / Reflux View Scheme
Multi-step reaction with 9 steps 1.1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate 2.1: hydrogen bromide / water; acetic acid / 8 h / Reflux 3.1: pyridine / dichloromethane / 1 h / -78 - 0 °C 4.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere 5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 0.92 h / 0 °C / Reflux 6.1: methanol / 1 h / Reflux 7.1: dmap; triethylamine / dichloromethane / 4 h / 20 °C 8.1: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere; Sonication 9.1: hydrogenchloride / ethanol; water / 1 h / 20 °C 9.2: pH 8 - 9 View Scheme

Yield

Multi-step reaction with 7 steps
1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate
2: hydrogen bromide / water; acetic acid / 8 h / Reflux
3: pyridine / dichloromethane / 1 h / -78 - 0 °C
4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere
5: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 1 h / 80 °C / Inert atmosphere
6: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 1,2-dichloro-ethane / 19.33 h / 0 - 20 °C
7: methanol / 1 h / Reflux
View Scheme

Multi-step reaction with 9 steps
1.1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate
2.1: hydrogen bromide / water; acetic acid / 8 h / Reflux
3.1: pyridine / dichloromethane / 1 h / -78 - 0 °C
4.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere
5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 0.92 h / 0 °C / Reflux
6.1: methanol / 1 h / Reflux
7.1: dmap; triethylamine / dichloromethane / 4 h / 20 °C
8.1: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere; Sonication
9.1: hydrogenchloride / ethanol; water / 1 h / 20 °C
9.2: pH 8 - 9
View Scheme

: 67165-56-4
Diclofensine

: 1254942-01-2
tert-butyl 7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate 2: hydrogen bromide / water; acetic acid / 8 h / Reflux 3: pyridine / dichloromethane / 1 h / -78 - 0 °C 4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere 5: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 1 h / 80 °C / Inert atmosphere 6: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 1,2-dichloro-ethane / 19.33 h / 0 - 20 °C 7: methanol / 1 h / Reflux 8: N,N-dimethyl-formamide / 1 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate 2: hydrogen bromide / water; acetic acid / 8 h / Reflux 3: pyridine / dichloromethane / 1 h / -78 - 0 °C 4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere 5: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 0.92 h / 0 °C / Reflux 6: methanol / 1 h / Reflux 7: dmap; triethylamine / dichloromethane / 4 h / 20 °C 8: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere; Sonication View Scheme

Yield

Multi-step reaction with 8 steps
1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate
2: hydrogen bromide / water; acetic acid / 8 h / Reflux
3: pyridine / dichloromethane / 1 h / -78 - 0 °C
4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere
5: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 1 h / 80 °C / Inert atmosphere
6: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 1,2-dichloro-ethane / 19.33 h / 0 - 20 °C
7: methanol / 1 h / Reflux
8: N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme

Multi-step reaction with 8 steps
1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate
2: hydrogen bromide / water; acetic acid / 8 h / Reflux
3: pyridine / dichloromethane / 1 h / -78 - 0 °C
4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere
5: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 0.92 h / 0 °C / Reflux
6: methanol / 1 h / Reflux
7: dmap; triethylamine / dichloromethane / 4 h / 20 °C
8: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere; Sonication
View Scheme

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Specification

The Diclofensine, with the CAS registry number 67165-56-4, is also known as 4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-7-methoxy-2-methylisoquinoline. It belongs to the product categories of Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C₁₇H₁₇Cl₂NO and molecular weight is 322.23. What's more, its systematic name is 4-(3,4-Dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline. It is a stimulant which can inhibits reuptake of dopamine and noradrenaline, and it is also an effective antidepressant.

Physical properties of Diclofensine are: (1)ACD/LogP: 3.685; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.39; (4)ACD/LogD (pH 7.4): 3.09; (5)ACD/BCF (pH 5.5): 1.89; (6)ACD/BCF (pH 7.4): 95.17; (7)ACD/KOC (pH 5.5): 12.25; (8)ACD/KOC (pH 7.4): 615.99; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 12.47 Å²; (13)Index of Refraction: 1.591; (14)Molar Refractivity: 87.614 cm³; (15)Molar Volume: 259.405 cm³; (16)Polarizability: 34.733×10^-24cm³; (17)Surface Tension: 42.8289985656738 dyne/cm; (18)Density: 1.242 g/cm³; (19)Flash Point: 209.378 °C; (20)Enthalpy of Vaporization: 67.679 kJ/mol; (21)Boiling Point: 422.595 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1ccc(cc1Cl)C3c2ccc(OC)cc2CN(C3)C
(2)Std. InChI: InChI=1S/C17H17Cl2NO/c1-20-9-12-7-13(21-2)4-5-14(12)15(10-20)11-3-6-16(18)17(19)8-11/h3-8,15H,9-10H2,1-2H3
(3)Std. InChIKey: ZJDCGVDEEHWEIG-UHFFFAOYSA-N