3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate

Base Information

• Chemical Name: 3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate
• CAS No.: 1295642-84-0
• Molecular Formula: C₄₁H₅₆N₄O₆
• Molecular Weight: 700.919

Synonyms:3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate

Chemical Property of 3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate

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Technology Process of 3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate

There total 13 articles about 3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate 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:

8‐(2‐aminoethyl)‐5‐hydroxy‐2H‐benzo[b][1,4]oxazin‐3(4H)‐one hydrochloride (1035229-35-6) + N-(2,2-dimethoxyethyl)-3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-((R)-1-methylpentyl)propionamide (1295645-14-5) → 3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate (1295642-84-0)

Guidance literature:

N-(2,2-dimethoxyethyl)-3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-((R)-1-methylpentyl)propionamide; With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 0.75h;

8‐(2‐aminoethyl)‐5‐hydroxy‐2H‐benzo[b][1,4]oxazin‐3(4H)‐one hydrochloride; With sodium hydrogencarbonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water; for 0.166667h;

With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water; at 20 ℃; for 18h;

Reference yield:

4-hydroxy-4-phenylpiperidin (40807-61-2) → 3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate (1295642-84-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: trifluorormethanesulfonic acid / nitrobenzene / 0 - 20 °C

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / -5 °C / Inert atmosphere

4.2: Cooling

5.1: N-benzyl-trimethylammonium hydroxide / toluene; methanol

5.2: 0 - 20 °C

6.1: dichloromethane / 2 h / 20 °C

7.1: water / 1,2-dichloro-ethane / 0.17 h

7.2: 16 h

8.1: hydrogen / palladium on carbon / ethanol / 16 h / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h

9.2: 18 h / 20 °C

10.1: toluene-4-sulfonic acid / tetrahydrofuran / 0.75 h / 20 °C

10.2: 0.17 h

10.3: 18 h / 20 °C

With lithium aluminium tetrahydride; trifluorormethanesulfonic acid; water; hydrogen; N-benzyl-trimethylammonium hydroxide; caesium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; palladium on carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; nitrobenzene; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

Reference yield:

[4-hydroxy-3-(4-phenylpiperidin-4-yl)phenyl]acetic acid methyl ester (1295644-32-4) → 3-{2-[4-hydroxy-3-(1-methyl-4-phenylpiperidin-4-yl)phenyl]ethoxy}-N-{2-[2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)ethylamino]ethyl}-N-((R)-1-methylpentyl)propionamide diformate (1295642-84-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C

2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 50 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / -5 °C / Inert atmosphere

3.2: Cooling

4.1: N-benzyl-trimethylammonium hydroxide / toluene; methanol

4.2: 0 - 20 °C

5.1: dichloromethane / 2 h / 20 °C

6.1: water / 1,2-dichloro-ethane / 0.17 h

6.2: 16 h

7.1: hydrogen / palladium on carbon / ethanol / 16 h / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h

8.2: 18 h / 20 °C

9.1: toluene-4-sulfonic acid / tetrahydrofuran / 0.75 h / 20 °C

9.2: 0.17 h

9.3: 18 h / 20 °C

With lithium aluminium tetrahydride; water; hydrogen; N-benzyl-trimethylammonium hydroxide; caesium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; palladium on carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

4-hydroxy-4-phenylpiperidin

Methyl 4-hydroxyphenylacetate

(R)‐2‐aminohexane

8‐(2‐aminoethyl)‐5‐hydroxy‐2H‐benzo[b][1,4]oxazin‐3(4H)‐one hydrochloride

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