3-methoxybenzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate

Base Information

• Chemical Name: 3-methoxybenzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate
• CAS No.: 1416051-69-8
• Molecular Formula: C₂₂H₂₃NO₄S
• Molecular Weight: 397.495
• Mol file: 1416051-69-8.mol

Synonyms:

Chemical Property of 3-methoxybenzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methoxybenzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate

There total 4 articles about 3-methoxybenzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate 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: 18.0%

tert-butyl 4-((2-(((3-methoxybenzyl)oxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate (1416051-66-5) → 3-methoxybenzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate (1416051-69-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jm301474t

Reference yield:

Methyl thiosalicylate (4892-02-8) → 3-methoxybenzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate (1416051-69-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0.28 h / 0 - 20 °C

2.1: triphenylphosphine / tetrahydrofuran / 0.33 h / Inert atmosphere

2.2: Mitsunobu Displacement / 1.58 h / 0 - 20 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate / methanol / 3 h / 20 °C

4.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 0.25 h / 20 °C

4.2: 18 h / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With lithium hydroxide monohydrate; potassium tert-butylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: |Dieckmann Condensation / 2.1: |Mitsunobu Displacement;

DOI:10.1021/jm301474t

Reference yield:

3-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)benzo[b]thiophene-2-carboxylic acid (1416051-63-2) → 3-methoxybenzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate (1416051-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 0.25 h / 20 °C

1.2: 18 h / 20 °C

2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1021/jm301474t

upstream raw materials:

tert-butyl 4-((2-(((3-methoxybenzyl)oxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate

Methyl thiosalicylate

3-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)benzo[b]thiophene-2-carboxylic acid