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866783-13-3

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Basic Information
CAS No.: 866783-13-3
Name: (1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride
Article Data: 6
Molecular Structure:
Molecular Structure of 866783-13-3 ((1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride)
Formula: C12H18ClNO2
Molecular Weight: 243.733
Synonyms: Bicyclo[4.2.0]octa-1,3,5-triene-7-methanamine,3,4-dimethoxy-N-methyl-, hydrochloride, (7S)- (9CI);(1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride;(S)-N-[（4,5-dimethoxybenzocyclobut-1-yl）methyl ]-N-methylamine hydrochloride;
EINECS: 617-905-7
Boiling Point: 338.6 °C at 760 mmHg
Flash Point: 158.6 °C
PSA: 30.49000
LogP: 2.75580
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Synthetic route
866783-12-2

[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Stage #1: [{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine With acetic acid In ethanol at 20℃; for 0.5h;
Stage #2: With hydrogenchloride at 15 - 20℃; for 1h;		95%
With hydrogenchloride In ethanol; ethyl acetate at 15 - 20℃; for 1h; Industry scale;92%
1031767-75-5

[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine d-camphorsulfonate

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Stage #1: [{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine d-camphorsulfonate In dichloromethane; water pH=10 - 11;
Stage #2: With hydrogenchloride In ethanol; ethyl acetate at 0 - 5℃; pH=1 - 2;		94%
1220993-43-0

(7S)-3,4-dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-carboxamide

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Stage #1: (7S)-3,4-dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-carboxamide With borane-THF In tetrahydrofuran at 20 - 50℃;
Stage #2: With methanol In tetrahydrofuran at 0 - 5℃; for 0.25h;
Stage #3: With hydrogenchloride In ethyl acetate at 0℃; for 2.5h; Reflux;		88%
Stage #1: (7S)-3,4-dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-carboxamide With borane-THF In tetrahydrofuran at 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol for 4h;		77%
148870-55-7

ethyl ((3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl)carbamate

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Stage #1: ethyl [(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl]carbamate With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Reflux;
Stage #2: With hydrogenchloride In ethanol; ethyl acetate at 15 - 20℃; for 1h;		85%
35202-54-1

3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium hydroxide; water / 4 h / Reflux
1.2: 20 °C
2.1: ethyl acetate / 1.25 h / 0 °C / Reflux
3.1: hydrogenchloride / dichloromethane; water / 0.08 h
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
5.1: dichloromethane; water / 0 - 10 °C
6.1: borane-THF / tetrahydrofuran / 20 - 50 °C
6.2: 0.25 h / 0 - 5 °C
6.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 6 steps
1.1: potassium hydroxide; water / 4 h / Reflux
1.2: 20 °C
2.1: acetone / 0.5 h / Reflux; Cooling
3.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
5.1: dichloromethane; water / 0 - 10 °C
6.1: borane-THF / tetrahydrofuran / 20 - 50 °C
6.2: 0.25 h / 0 - 5 °C
6.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 6 steps
1.1: potassium hydroxide; water / 4 h / Reflux
1.2: 20 °C
2.1: ethyl acetate / 1 h / 18 °C / Heating
3.1: hydrogenchloride / dichloromethane; water / 0.33 h
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
5.1: dichloromethane; water / 0 - 10 °C
6.1: borane-THF / tetrahydrofuran / 20 - 50 °C
6.2: 0.25 h / 0 - 5 °C
6.3: 2.5 h / 0 °C / Reflux
View Scheme
41234-23-5

(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ethyl acetate / 1.25 h / 0 °C / Reflux
2.1: hydrogenchloride / dichloromethane; water / 0.08 h
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: ethyl acetate / 1 h / 18 °C / Heating
2.1: hydrogenchloride / dichloromethane; water / 0.33 h
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: ethyl acetate / 1 h / 18 °C / Heating
2.1: hydrogenchloride / dichloromethane; water / 0.33 h
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: ethyl acetate / Heating
2.1: hydrogenchloride / dichloromethane; water / 0.33 h
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: acetone / 0.5 h / Reflux; Cooling
2.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
4.1: dichloromethane; water / 0 - 10 °C
5.1: borane-THF / tetrahydrofuran / 20 - 50 °C
5.2: 0.25 h / 0 - 5 °C
5.3: 2.5 h / 0 °C / Reflux
View Scheme

(S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid (+)-cinchonine

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride / dichloromethane; water / 0.08 h
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
3.1: dichloromethane; water / 0 - 10 °C
4.1: borane-THF / tetrahydrofuran / 20 - 50 °C
4.2: 0.25 h / 0 - 5 °C
4.3: 2.5 h / 0 °C / Reflux
View Scheme
1220993-44-1

(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
2.1: dichloromethane; water / 0 - 10 °C
3.1: borane-THF / tetrahydrofuran / 20 - 50 °C
3.2: 0.25 h / 0 - 5 °C
3.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 20 °C
1.2: 20 °C
2.1: borane-THF / tetrahydrofuran / 20 °C
2.2: 4 h
View Scheme
1346558-07-3

(S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid (S)-(-)-1-(naphthyl)-ethylamine

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride / dichloromethane; water / 0.33 h
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
3.1: dichloromethane; water / 0 - 10 °C
4.1: borane-THF / tetrahydrofuran / 20 - 50 °C
4.2: 0.25 h / 0 - 5 °C
4.3: 2.5 h / 0 °C / Reflux
View Scheme

3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid (S)-(-)-1-(naphthyl)-ethylamine

866783-13-3

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride / dichloromethane; water / 0.33 h
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
3.1: dichloromethane; water / 0 - 10 °C
4.1: borane-THF / tetrahydrofuran / 20 - 50 °C
4.2: 0.25 h / 0 - 5 °C
4.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 7 steps
1.1: hydrogenchloride / dichloromethane; water / 0.33 h
2.1: potassium hydroxide / water / 4 h
2.2: 0.5 h / Cooling with ice-water bath
3.1: acetone / 0.5 h / Reflux; Cooling
4.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3
5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
6.1: dichloromethane; water / 0 - 10 °C
7.1: borane-THF / tetrahydrofuran / 20 - 50 °C
7.2: 0.25 h / 0 - 5 °C
7.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 7 steps
1.1: hydrogenchloride / dichloromethane; water / 0.33 h
2.1: potassium hydroxide / water / 4 h
2.2: 0.5 h / Cooling with ice-water bath
3.1: ethyl acetate / 1.25 h / 0 °C / Reflux
4.1: hydrogenchloride / dichloromethane; water / 0.08 h
5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
6.1: dichloromethane; water / 0 - 10 °C
7.1: borane-THF / tetrahydrofuran / 20 - 50 °C
7.2: 0.25 h / 0 - 5 °C
7.3: 2.5 h / 0 °C / Reflux
View Scheme
Multi-step reaction with 7 steps
1.1: hydrogenchloride / dichloromethane; water / 0.33 h
2.1: potassium hydroxide / water / 4 h
2.2: 0.5 h / Cooling with ice-water bath
3.1: ethyl acetate / Heating
4.1: hydrogenchloride / dichloromethane; water / 0.33 h
5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
6.1: dichloromethane; water / 0 - 10 °C
7.1: borane-THF / tetrahydrofuran / 20 - 50 °C
7.2: 0.25 h / 0 - 5 °C
7.3: 2.5 h / 0 °C / Reflux
View Scheme
Raw Materials
35202-54-1
866783-12-2
41234-23-5
35249-62-8
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148849-67-6
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Chemistry

Molecular Structure of Bicyclo[4.2.0]octa-1,3,5-triene-7-methanamine,3,4-dimethoxy-N-methyl-, hydrochloride (1:1), (7S)- (CAS NO.866783-13-3):

Systematic Name: 1-[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride  
Empirical Formula: C12H18ClNO2
Molecular Weight: 243.7298
Nominal Mass: 243
Average Mass: 243.7298
Monoisotopic Mass: 243.102607 
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 4
Flash Point: 158.6 °C
Enthalpy of Vaporization: 59.35 kJ/mol
Boiling Point: 338.6 °C at 760 mmHg
Vapour Pressure: 6.95E-05 mmHg at 25 °C
SMILES: Cl.O(c1cc2c(cc1OC)[C@@H](CNC)C2)C
InChI: InChI=1/C12H17NO2.ClH/c1-13-7-9-4-8-5-11(14-2)12(15-3)6-10(8)9;/h5-6,9,13H,4,7H2,1-3H3;1H/t9-;/m1./s1
InChIKey: SWSAIQSQSDOONK-SBSPUUFOBL

Specification

 Bicyclo[4.2.0]octa-1,3,5-triene-7-methanamine,3,4-dimethoxy-N-methyl-, hydrochloride (1:1), (7S)- (CAS NO.866783-13-3), its Synonyms are (7S)-3,4-Dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-methanamine hydrochloride ; (1S)-4,5-Dimethoxy-1-[(methylamino)methyl]benzocyclobutane hydrochloride .