Product Name

  • Name

    Amorolfine

  • EINECS
  • CAS No. 78613-35-1
  • Article Data6
  • CAS DataBase
  • Density 0.925 g/cm3
  • Solubility
  • Melting Point 134oC
  • Formula C21H35NO
  • Boiling Point 407.077 °C at 760 mmHg
  • Molecular Weight 317.515
  • Flash Point 119.612 °C
  • Transport Information
  • Appearance white to off-white crystalline powder
  • Safety 26-36
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 78613-35-1 (Amorolfine)
  • Hazard Symbols HarmfulXn
  • Synonyms Morpholine,4-[3-[4-(1,1-dimethylpropyl)phenyl]-2-methylpropyl]-2,6-dimethyl-, cis-;Loceryl;Ro 14-4767;Ro 14-4767/000;(+/-)-cis-2,6-Dimethyl-4-[2-methyl-3-(p-tert-pentylphenyl)propyl]morpholine;
  • PSA 12.47000
  • LogP 4.59990

Synthetic route

C21H33NO2

C21H33NO2

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 30℃; Reagent/catalyst; Inert atmosphere;93%
tert-Amyl alcohol
75-85-4

tert-Amyl alcohol

(2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride
922734-43-8

(2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Stage #1: (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride With sulfuric acid In dichloromethane at -10℃; for 0.166667h;
Stage #2: tert-Amyl alcohol In dichloromethane at -10 - 20℃;		91.64%
sulfuric acid In dichloromethane at -5℃; for 1h; Friedel Crafts Alkylation;
amorolfine hydrochloride

amorolfine hydrochloride

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water pH=13; Product distribution / selectivity;90%
C16H26O3S

C16H26O3S

cis-2,6-dimethylmorpholine
141-91-3, 6485-45-6, 6485-55-8

cis-2,6-dimethylmorpholine

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
With triethylamine In toluene at 25℃; for 8h; Solvent; Reagent/catalyst;87%
2-methyl-2-butylchloride
594-36-5

2-methyl-2-butylchloride

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Stage #1: (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride With iron(III) chloride In dichloromethane
Stage #2: 2-methyl-2-butylchloride In dichloromethane at -20 - 20℃;
Stage #3: With sodium hydroxide; water Product distribution / selectivity; more than 3 stages;		8%
Multi-step reaction with 4 steps
1.1: iron(III) chloride / dichloromethane / 0 - 5 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dimethyl sulfoxide / 1 h / 25 - 30 °C
2.2: 25 - 30 °C
3.1: palladium on activated charcoal; hydrogen / ethanol / 35 - 40 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 30 °C / Inert atmosphere
View Scheme
2-methyl-2-butylchloride
594-36-5

2-methyl-2-butylchloride

A

amorolfine
78613-35-1

amorolfine

B

cis-4-<3-(4-tert-butylphenyl)-2-methylpropyl>-2,6-dimethylmorpholine
67564-91-4

cis-4-<3-(4-tert-butylphenyl)-2-methylpropyl>-2,6-dimethylmorpholine

Conditions
ConditionsYield
Stage #1: (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride With iron(III) chloride In dichloromethane
Stage #2: 2-methyl-2-butylchloride In dichloromethane at -52 - -20℃;
Stage #3: With sodium hydroxide; water Product distribution / selectivity; more than 3 stages;		A n/a
B 0.14%
(2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride
922734-43-8

(2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride

2-methyl-2-butylchloride
594-36-5

2-methyl-2-butylchloride

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Stage #1: (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride; Friedel-Craft catalyst In dichloromethane at -20℃;
Stage #2: 2-methyl-2-butylchloride In dichloromethane Reactivity (does not react); Friedel Crafts Alkylation;
Stage #1: (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride; Friedel-Craft catalyst In dichloromethane at 0 - 30℃;
Stage #2: 2-methyl-2-butylchloride In dichloromethane Product distribution / selectivity; Friedel Crafts Alkylation;
Stage #1: (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride; Friedel-Craft catalyst In dichloromethane at 20 - 30℃;
Stage #2: 2-methyl-2-butylchloride In dichloromethane at -50℃; for 2.5h; Friedel Crafts Alkylation;
Stage #3: With hydrogenchloride; sodium hydroxide Product distribution / selectivity; more than 3 stages;
Stage #1: (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride; iron(III) chloride In dichloromethane at 33℃; for 0.166667h; Friedel Crafts Alkylation;
Stage #2: 2-methyl-2-butylchloride In dichloromethane at -20℃; for 2.5h; Product distribution / selectivity;
(2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride
922734-43-8

(2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride

2-methyl-2-butylchloride
594-36-5

2-methyl-2-butylchloride

A

amorolfine
78613-35-1

amorolfine

B

cis-4-<3-(4-tert-butylphenyl)-2-methylpropyl>-2,6-dimethylmorpholine
67564-91-4

cis-4-<3-(4-tert-butylphenyl)-2-methylpropyl>-2,6-dimethylmorpholine

Conditions
ConditionsYield
Stage #1: (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride; Friedel-Craft catalyst In dichloromethane
Stage #2: 2-methyl-2-butylchloride In dichloromethane at -52 - -20℃; Product distribution / selectivity; Friedel Crafts Alkylation;
...Expand
2-methyl-3-phenylacrylic acid
1895-97-2

2-methyl-3-phenylacrylic acid

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: magnesium / methanol / 60 - 70 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 35 °C
3.2: pH 3 - 4
4.1: sulfuric acid / dichloromethane / 0.17 h / -10 °C
4.2: -10 - 20 °C
View Scheme
cis-2,6-dimethylmorpholine
141-91-3, 6485-45-6, 6485-55-8

cis-2,6-dimethylmorpholine

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: magnesium / methanol / 60 - 70 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 35 °C
3.2: pH 3 - 4
4.1: sulfuric acid / dichloromethane / 0.17 h / -10 °C
4.2: -10 - 20 °C
View Scheme
C16H21NO2

C16H21NO2

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium / methanol / 60 - 70 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 35 °C
2.2: pH 3 - 4
3.1: sulfuric acid / dichloromethane / 0.17 h / -10 °C
3.2: -10 - 20 °C
View Scheme
C16H23NO2

C16H23NO2

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 35 °C
1.2: pH 3 - 4
2.1: sulfuric acid / dichloromethane / 0.17 h / -10 °C
2.2: -10 - 20 °C
View Scheme
α-methylcinnamic acid
1199-77-5

α-methylcinnamic acid

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: iron(III) chloride / dichloromethane / 0 - 5 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dimethyl sulfoxide / 1 h / 25 - 30 °C
2.2: 25 - 30 °C
3.1: palladium on activated charcoal; hydrogen / ethanol / 35 - 40 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 30 °C / Inert atmosphere
View Scheme
C15H20O2

C15H20O2

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dimethyl sulfoxide / 1 h / 25 - 30 °C
1.2: 25 - 30 °C
2.1: palladium on activated charcoal; hydrogen / ethanol / 35 - 40 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 30 °C / Inert atmosphere
View Scheme
C21H31NO2

C21H31NO2

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium on activated charcoal; hydrogen / ethanol / 35 - 40 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 30 °C / Inert atmosphere
View Scheme
2-methyl-3-(4-tert-amylphenyl)propanol

2-methyl-3-(4-tert-amylphenyl)propanol

amorolfine
78613-35-1

amorolfine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / toluene / 6 h / 0 - 25 °C / Large scale
2: triethylamine / toluene / 8 h / 25 °C
View Scheme
amorolfine
78613-35-1

amorolfine

amorolfine hydrochloride

amorolfine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0 - 5℃; pH=3 - 4;94%
amorolfine
78613-35-1

amorolfine

amorolfine hydrochloride

amorolfine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 20℃; for 0.5h; pH=3 - 4;93.36%
With hydrogenchloride In Isopropyl acetate at 0℃; pH=3 - 4; Large scale;80%
With hydrogenchloride In ethanol at 10 - 65℃; pH=1.5 - 3;77%
With hydrogenchloride In ethanol at -20 - 65℃; for 0.5 - 2h;77%
With hydrogenchloride In isopropyl alcohol

Amorolfine Specification

The Amorolfine, with the CAS registry number 78613-35-1, is also known as (+/-)-cis-2,6-Dimethyl-4-[2-methyl-3-(p-tert-pentylphenyl)propyl]morpholine. This chemical's molecular formula is C21H35NO and molecular weight is 317.51. What's more, its systematic name is (2R,6S)-2,6-Dimethyl-4-{2-methyl-3-[4-(2-methyl-2-butanyl)phenyl]propyl}morpholine. Its classification code is Antimycotic. This chemical is a morpholine antifungal drug that inhibits D14 reductase and D7-D8 isomerase, which depletes ergosterol and causes ignosterol to accumulate in the fungal cytoplasmic cell membranes.

Physical properties of Amorolfine are: (1)ACD/LogP: 5.636; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.82; (4)ACD/LogD (pH 7.4): 5.37; (5)ACD/BCF (pH 5.5): 172.03; (6)ACD/BCF (pH 7.4): 6085.90; (7)ACD/KOC (pH 5.5): 421.85; (8)ACD/KOC (pH 7.4): 14923.66; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 12.47 Å2; (13)Index of Refraction: 1.489; (14)Molar Refractivity: 99.093 cm3; (15)Molar Volume: 343.401 cm3; (16)Polarizability: 39.284×10-24cm3; (17)Surface Tension: 30.99 dyne/cm; (18)Density: 0.925 g/cm3; (19)Flash Point: 119.612 °C; (20)Enthalpy of Vaporization: 65.89 kJ/mol; (21)Boiling Point: 407.077 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: O2[C@@H](CN(CC(C)Cc1ccc(cc1)C(C)(C)CC)C[C@@H]2C)C
(2)Std. InChI: InChI=1S/C21H35NO/c1-7-21(5,6)20-10-8-19(9-11-20)12-16(2)13-22-14-17(3)23-18(4)15-22/h8-11,16-18H,7,12-15H2,1-6H3/t16?,17-,18+
(3)Std. InChIKey: MQHLMHIZUIDKOO-AYHJJNSGSA-N 

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