(2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride

Base Information

• Chemical Name: (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride
• CAS No.: 1208110-14-8
• Molecular Formula: C₂₃H₂₆FNO₂*ClH
• Molecular Weight: 403.924
• Mol file: 1208110-14-8.mol

Synonyms:(2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride

Chemical Property of (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride

There total 22 articles about (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one 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: 100.0%

(2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1Hspiro[naphthalene-2,2'-piperidin]-1-one (1208110-12-6) → (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride (1208110-14-8)

Guidance literature:

With hydrogenchloride; In diethyl ether; water; ethyl acetate; Cooling with ice;

DOI:10.1016/j.bmc.2017.05.012

Reference yield:

(2RS)-1-benzoylpiperidine-2-carbonitrile (71413-04-2) → (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride (1208110-14-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 3.25 h / -78 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / toluene / 4 h / 20 °C

2.2: 18 h / 120 °C

3.1: di-isopropyl ether; ethanol / 18 h / 20 °C

4.1: sodium hydroxide / ethyl acetate

5.1: potassium carbonate; N-ethyl-N,N-diisopropylamine / toluene / 1 h / 20 °C

5.2: 72 h / Reflux

6.1: hydrogenchloride / ethyl acetate; diethyl ether; water / Cooling with ice

With hydrogenchloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; di-isopropyl ether; water; ethyl acetate; toluene;

DOI:10.1016/j.bmc.2017.05.012

Reference yield:

N-benzoyl-2-piperidinecarboxylic acid (78348-46-6) → (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride (1208110-14-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.5 h / -20 - -15 °C

1.2: 3 h / 20 °C

2.1: trichlorophosphate; pyridine / tetrahydrofuran; N,N-dimethyl-formamide / 27 h / 0 - 80 °C

3.1: lithium diisopropyl amide / tetrahydrofuran / 3.25 h / -78 - 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / toluene / 4 h / 20 °C

4.2: 18 h / 120 °C

5.1: di-isopropyl ether; ethanol / 18 h / 20 °C

6.1: sodium hydroxide / ethyl acetate

7.1: potassium carbonate; N-ethyl-N,N-diisopropylamine / toluene / 1 h / 20 °C

7.2: 72 h / Reflux

8.1: hydrogenchloride / ethyl acetate; diethyl ether; water / Cooling with ice

With pyridine; hydrogenchloride; chloroformic acid ethyl ester; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; diethyl ether; ethanol; di-isopropyl ether; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2017.05.012

upstream raw materials:

1-fluoro-3-(2-iodoethyl)benzene

(2RS)-1-benzoylpiperidine-2-carbonitrile

N-benzoyl-2-piperidinecarboxylic acid

3-methoxyphenethyl iodide

Refernces