4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone

Base Information

• Chemical Name: 4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone
• CAS No.: 412010-99-2
• Molecular Formula: C₁₈H₂₂ClNO₅
• Molecular Weight: 367.829
• Mol file: 412010-99-2.mol

Synonyms:4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone

Chemical Property of 4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone

There total 12 articles about 4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone 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: 66.0%

2-chloro-1,1,1-trimethoxyethane (74974-54-2) + 3-(Hydroxymethyl)-4-(2,3-dimethoxyphenyl)-1-methyl-5,6-dihydro-2-pyridinone (79619-02-6) → 4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone (412010-99-2)

Guidance literature:

With Trimethylacetic acid; In diethylene glycol dimethyl ether; 1.) 8 h, 165 deg C, 2.) 16 h, reflux;

DOI:10.1021/jo00338a003

Reference yield:

(E)-ethyl 3-(2,3-dimethoxyphenyl)prop-2-enoate (79618-90-9) → 4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone (412010-99-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaOEt / 1.) EtOH, 2.) EtOH, 3 h, reflux

2: H₂, ethanolic HCl / PtO₂ / 12 h / 20 - 26 °C / 2068.6 - 2585.7 Torr

3: toluene / 2 h / Heating

4: 1.) Me₃OBF₄, 2.) NaBH₄ / 1.) CH₂Cl₂, 24 h, room temperature, 2.) EtOH, 12 h, 23 deg C

5: 94 percent / H₂ / 10percent Pd/C / ethanol; H₂O / 24 h / 20 - 26 °C / 2068.6 - 2585.7 Torr

7: 55 percent / SeO₂ / chlorobenzene / 1.17 h / 100 °C

8: 85 percent / 16 h / Ambient temperature

9: K₂CO₃, MeOH / 22 h / Ambient temperature

10: 66 percent / pivalic acid / bis-(2-methoxy-ethyl) ether / 1.) 8 h, 165 deg C, 2.) 16 h, reflux

With hydrogenchloride; methanol; sodium tetrahydroborate; selenium(IV) oxide; hydrogen; sodium ethanolate; trimethoxonium tetrafluoroborate; potassium carbonate; Trimethylacetic acid; platinum(IV) oxide; palladium on activated charcoal; In ethanol; diethylene glycol dimethyl ether; water; chlorobenzene; toluene;

DOI:10.1021/jo00338a003

Reference yield:

3-methoxy-2-hydroxybenzaldehyde (148-53-8) → 4-<(Methoxycarbonyl)chloromethyl>-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone (412010-99-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / K₂CO₃ / methanol / 2.5 h / Heating

2: 95 percent / piperidine / pyridine / 7 h / Heating

3: 1.) NaOEt / 1.) EtOH, 2.) EtOH, 3 h, reflux

4: H₂, ethanolic HCl / PtO₂ / 12 h / 20 - 26 °C / 2068.6 - 2585.7 Torr

5: toluene / 2 h / Heating

6: 1.) Me₃OBF₄, 2.) NaBH₄ / 1.) CH₂Cl₂, 24 h, room temperature, 2.) EtOH, 12 h, 23 deg C

7: 94 percent / H₂ / 10percent Pd/C / ethanol; H₂O / 24 h / 20 - 26 °C / 2068.6 - 2585.7 Torr

9: 55 percent / SeO₂ / chlorobenzene / 1.17 h / 100 °C

10: 85 percent / 16 h / Ambient temperature

11: K₂CO₃, MeOH / 22 h / Ambient temperature

12: 66 percent / pivalic acid / bis-(2-methoxy-ethyl) ether / 1.) 8 h, 165 deg C, 2.) 16 h, reflux

With piperidine; hydrogenchloride; methanol; sodium tetrahydroborate; selenium(IV) oxide; hydrogen; sodium ethanolate; trimethoxonium tetrafluoroborate; potassium carbonate; Trimethylacetic acid; platinum(IV) oxide; palladium on activated charcoal; In pyridine; methanol; ethanol; diethylene glycol dimethyl ether; water; chlorobenzene; toluene;

DOI:10.1021/jo00338a003

upstream raw materials:

2-chloro-1,1,1-trimethoxyethane

3-(Hydroxymethyl)-4-(2,3-dimethoxyphenyl)-1-methyl-5,6-dihydro-2-pyridinone

(E)-ethyl 3-(2,3-dimethoxyphenyl)prop-2-enoate

4-Hydroxy-4-(2,3-dimethoxyphenyl)-1-methyl-3-methylene-2-piperidinone

Downstream raw materials:

4-(2,3-Dimethoxyphenyl)-1,3-dimethyl-2-piperidinone