2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide

Base Information

• Chemical Name: 2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide
• CAS No.: 1283095-60-2
• Molecular Formula: C₂₂H₂₆ClFN₂O₂S
• Molecular Weight: 436.978

Synonyms:2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide

Chemical Property of 2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide

Chemical Property:

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Technology Process of 2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide

There total 8 articles about 2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide 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: 75.0%

2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)propanoic acid (1283095-55-5) + methylamine hydrochloride (593-51-1) → 2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide (1283095-60-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jm101487v

Reference yield:

tert-butyl-4′,5′-dihydro-1H-spiro[piperidine-4,7′-thieno[2,3-c]pyran]-1-carboxylate (1283095-48-6) → 2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide (1283095-60-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 20 °C

3.1: triethylamine / tetrahydrofuran / 20 h / 65 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C

4.2: 0.5 h / -78 °C

4.3: 1 h / -78 - 0 °C

5.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

With hydrogenchloride; n-butyllithium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;

DOI:10.1021/jm101487v

Reference yield:

4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] (1283095-47-5) → 2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide (1283095-60-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / dichloromethane / 5 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 20 °C

4.1: triethylamine / tetrahydrofuran / 20 h / 65 °C

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C

5.2: 0.5 h / -78 °C

5.3: 1 h / -78 - 0 °C

6.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C

7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

With hydrogenchloride; n-butyllithium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;

DOI:10.1021/jm101487v

upstream raw materials:

3-(2-hydroxyethyl)thiophene

4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran]

tert-butyl-4′,5′-dihydro-1H-spiro[piperidine-4,7′-thieno[2,3-c]pyran]-1-carboxylate

t-butyl 2-fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4'-piperidine]-1'-carboxylate

Downstream raw materials:

(2R)-2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide

(2S)-2-[(2-chlorophenyl)methyl]-3-(2-fluorospiro[4,5-dihydrothieno-[2,3-c]pyran-7,4'-piperidine]-1'-yl)-N-methylpropanamide

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