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

Base Information

Chemical Name:1'-[2-(4-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride
CAS No.:1208109-85-6
Molecular Formula:C₂₃H₂₆FNO₂*ClH
Molecular Weight:403.924
Hs Code.:

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

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

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

There total 17 articles about 1'-[2-(4-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: 82.0%

: 173272-95-2
(2RS)-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one

: 164179-52-6
1-iodo-2-(4-fluorophenyl)ethane

: 1208109-85-6
1'-[2-(4-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride

Guidance literature:: (2RS)-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one; With sodium hydride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

1-iodo-2-(4-fluorophenyl)ethane; In N,N-dimethyl-formamide; at 120 ℃; for 6h;

With hydrogenchloride; In diethyl ether; water; ethyl acetate; Cooling with ice;
DOI:10.1016/j.bmc.2017.05.012

Reference yield:

: 34837-84-8
4-fluorobenzeneacetic acid methyl ester

: 1208109-85-6
1'-[2-(4-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4.5 h / 0 - 20 °C / Inert atmosphere

2.1: pyridine / 4 h / 0 - 20 °C

3.1: sodium iodide / acetone / 3 h / Reflux

4.1: sodium hydride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

4.2: 6 h / 120 °C

4.3: Cooling with ice

With pyridine; lithium aluminium tetrahydride; sodium hydride; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmc.2017.05.012

Reference yield:

: 78348-46-6
N-benzoyl-2-piperidinecarboxylic acid

: 1208109-85-6
1'-[2-(4-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride

Guidance literature:: Multi-step reaction with 5 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: trimethylsilyl trifluoromethanesulfonate / 18 h / 20 °C

4.2: 48 h / 130 °C

5.1: sodium hydride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

5.2: 6 h / 120 °C

5.3: Cooling with ice

With pyridine; trimethylsilyl trifluoromethanesulfonate; chloroformic acid ethyl ester; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2017.05.012