5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

Base Information

• Chemical Name: 5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride
• CAS No.: 79357-92-9
• Molecular Formula: C₁₉H₂₃NO₅*ClH
• Molecular Weight: 381.856
• Mol file: 79357-92-9.mol

Synonyms:5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

Chemical Property of 5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

There total 11 articles about 5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 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: 83.0%

5,8-dibenzyloxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (78311-08-7) → 5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (79357-92-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; water; for 20h; under 2941.2 Torr; Ambient temperature;

DOI:10.1248/cpb.29.744

Reference yield:

2,5-dihydroxybenzoic acid. (490-79-9) → 5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (79357-92-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / K₂CO₃ / dimethylformamide / 20 h / 100 °C

2: 65.6 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

3: 88.8 percent / SOCl₂ / benzene; CH₂Cl₂; pyridine / below 10 deg C, then 4 deg C, 1 h

4: 90.4 percent / dimethylsulfoxide / 3 h / Ambient temperature

5: 53.6 percent / 1.) NaBH₃(OCOCF₃); 1.) ethanolic HCl / tetrahydrofuran / 3 h / Ambient temperature

6: 72.8 percent / K₂CO₃ / benzene; CHCl₃; H₂O / below 5 deg C, then Rt, 3 h

7: POCl₃ / benzene / 4.5 h / Heating

8: NaBH₄ / methanol / 42 h / Ambient temperature

9: 83 percent / 1N HCl, H₂ / 10percent Pd-C / tetrahydrofuran; H₂O / 20 h / 2941.2 Torr / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; sodium (trifluoroacetoxy)borohydride; hydrogen; potassium carbonate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.29.744

Reference yield:

3,4,5-trimethoxyphenyl acetic acid (951-82-6) → 5,8-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (79357-92-9)

Guidance literature:

Multi-step reaction with 5 steps

1: SOCl₂ / benzene / 1 h / Heating

2: 72.8 percent / K₂CO₃ / benzene; CHCl₃; H₂O / below 5 deg C, then Rt, 3 h

3: POCl₃ / benzene / 4.5 h / Heating

4: NaBH₄ / methanol / 42 h / Ambient temperature

5: 83 percent / 1N HCl, H₂ / 10percent Pd-C / tetrahydrofuran; H₂O / 20 h / 2941.2 Torr / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; thionyl chloride; hydrogen; potassium carbonate; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; water; benzene;

DOI:10.1248/cpb.29.744

upstream raw materials:

5,8-dibenzyloxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

2,5-dihydroxybenzoic acid.

3,4,5-trimethoxyphenyl acetic acid

3,4,5-trimethoxyphenylacetyl chloride