1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran]

Base Information

• Chemical Name: 1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran]
• CAS No.: 1093379-00-0
• Molecular Formula: C₁₈H₂₅NOS
• Molecular Weight: 303.469
• Mol file: 1093379-00-0.mol

Synonyms:1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran]

Chemical Property of 1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran]

There total 14 articles about 1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran] 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: 43.0%

trimethylsilyl cyanide (7677-24-9) + 1-(cyclohexylmethyl)-6'-methoxy-6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran] (1070709-21-5) → 1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran] (1093379-00-0) + 1-(cyclohexylmethyl)-6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran]-6'-carbonitrile (1093379-01-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1021/jm300302p

Reference yield:

(E/Z)-3-bromo-2-(2-methoxyvinyl)thiophene → 1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran] (1093379-00-0) + 1-(cyclohexylmethyl)-6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran]-6'-carbonitrile (1093379-01-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / methanol / 24 h / Heating / reflux

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.28 - 0.3 h / -78 °C

2.2: 3.5 h / -78 - 20 °C

3.1: toluene-4-sulfonic acid; trimethyl orthoformate / methanol / 3 h / 20 °C

4.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 - 0 °C

With n-butyllithium; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; trimethyl orthoformate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane;

Reference yield:

2-(3-bromothiophen-2-yl)acetaldehyde dimethyl acetal (1070708-90-5) → 1-(cyclohexylmethyl)spiro[piperidine-4,4'-thieno[3,2-c]pyran] (1093379-00-0) + 1-(cyclohexylmethyl)-6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran]-6'-carbonitrile (1093379-01-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.28 - 0.3 h / -78 °C

1.2: 3.5 h / -78 - 20 °C

2.1: toluene-4-sulfonic acid; trimethyl orthoformate / methanol / 3 h / 20 °C

3.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -20 - 0 °C

With n-butyllithium; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; trimethyl orthoformate; In tetrahydrofuran; methanol; hexane; dichloromethane;

upstream raw materials:

trimethylsilyl cyanide

1-(cyclohexylmethyl)-6'-methoxy-6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran]

1-phenylmethyl-4-piperidone

2-(3-bromothiophen-2-yl)acetaldehyde dimethyl acetal

Downstream raw materials:

1-(cyclohexylmethyl)-6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran]