6-Chloro-2,3,4,5-tetrahydro-8-hydroxy-1-(4-hydroxyphenyl)-7-methoxy-1H-3-benzazepine hydrochloride

Base Information

• Chemical Name: 6-Chloro-2,3,4,5-tetrahydro-8-hydroxy-1-(4-hydroxyphenyl)-7-methoxy-1H-3-benzazepine hydrochloride
• CAS No.: 110038-80-7
• Molecular Formula: C₁₇H₁₈ClNO₃*ClH
• Molecular Weight: 356.249
• Mol file: 110038-80-7.mol

Synonyms:

Chemical Property of 6-Chloro-2,3,4,5-tetrahydro-8-hydroxy-1-(4-hydroxyphenyl)-7-methoxy-1H-3-benzazepine hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-Chloro-2,3,4,5-tetrahydro-8-hydroxy-1-(4-hydroxyphenyl)-7-methoxy-1H-3-benzazepine hydrochloride

There total 16 articles about 6-Chloro-2,3,4,5-tetrahydro-8-hydroxy-1-(4-hydroxyphenyl)-7-methoxy-1H-3-benzazepine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 37.0%

α-<<<2-<2-Chloro-4-hydroxy-3-methoxy>ethyl>amino>methyl>-4-hydroxybenzenemethanol hydrochloride (110039-02-6) → 6-Chloro-2,3,4,5-tetrahydro-8-hydroxy-1-(4-hydroxyphenyl)-7-methoxy-1H-3-benzazepine hydrochloride (110038-80-7)

Guidance literature:

With hydrogenchloride; trifluorormethanesulfonic acid; for 0.25h; 1.) trifluoroacetic acid, reflux, 15 min, 2.) ether;;

DOI:10.1002/jhet.5570230641

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → 6-Chloro-2,3,4,5-tetrahydro-8-hydroxy-1-(4-hydroxyphenyl)-7-methoxy-1H-3-benzazepine hydrochloride (110038-80-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / NH₄Cl / H₂O; diethyl ether / 24 h / Ambient temperature

2: 57 percent / 1.) borane, 2.) methanol, 3.) HCl gas / 1.) THF, reflux, 3.5 h, 2.) reflux 45 min, 3.) reflux, 15 h;

3: K₂CO₃ / H₂O; CH₂Cl₂; toluene / 1 h

4: 77 percent / 1.) borane-tetrahydrofuran, 2.) methanol; / Heating; 1.) THF, reflux, 1.5 h, 2.) reflux, 2 h;

5: 85 percent / H₂ / 10percent palladium on carbon / ethanol; methanol

6: 37 percent / 1.) trifluoromethanesulfonic acid, 2.) HCl; / 0.25 h / 1.) trifluoroacetic acid, reflux, 15 min, 2.) ether;

With hydrogenchloride; methanol; borane-THF; trifluorormethanesulfonic acid; borane; hydrogen; potassium carbonate; ammonium chloride; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; water; toluene;

DOI:10.1002/jhet.5570230641

Reference yield:

vanillin acetate (881-68-5) → 6-Chloro-2,3,4,5-tetrahydro-8-hydroxy-1-(4-hydroxyphenyl)-7-methoxy-1H-3-benzazepine hydrochloride (110038-80-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 81 percent / fuming HNO₃ / -20 °C

2: 79 percent / 1.) FeSO₄, aq. HCl, 2.) 15 N ammonium hydroxide; / 90 °C

3: 1.) aq. HCl, NaNO₂, 2.) Cu₂Cl₂; / 1.) water, 0 deg C, 2.) temperature below 5 deg C, 3.) heating on steam bath, 1 h;

4: 89 percent / NaBH₄ / propan-2-ol / 1 h / 70 °C

5: 60 percent / K₂CO₃ / dimethylformamide / 36 h / Ambient temperature

6: 100 percent / SOCl₂ / CH₂Cl₂ / 1.5 h / Heating

7: 64 percent / dimethylsulfoxide / 3 h / Ambient temperature

8: 87 percent / aq. 25percent NaOH / ethanol / Heating; overnight

9: SOCl₂ / CH₂Cl₂ / 2.5 h / Heating

10: K₂CO₃ / H₂O; CH₂Cl₂; toluene / 1 h

11: 77 percent / 1.) borane-tetrahydrofuran, 2.) methanol; / Heating; 1.) THF, reflux, 1.5 h, 2.) reflux, 2 h;

12: 85 percent / H₂ / 10percent palladium on carbon / ethanol; methanol

13: 37 percent / 1.) trifluoromethanesulfonic acid, 2.) HCl; / 0.25 h / 1.) trifluoroacetic acid, reflux, 15 min, 2.) ether;

With copper(I) chloride; hydrogenchloride; methanol; ammonium hydroxide; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; borane-THF; trifluorormethanesulfonic acid; hydrogen; nitric acid; potassium carbonate; iron(II) sulfate; sodium nitrite; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1002/jhet.5570230641

upstream raw materials:

α-<<<2-<2-Chloro-4-hydroxy-3-methoxy>ethyl>amino>methyl>-4-hydroxybenzenemethanol hydrochloride

p-benzyloxybenzaldehyde

vanillin acetate

α-Hydroxy-4-(phenylmethoxy)benzeneacetonitrile

Refernces