[1,4'-Bipiperidine]-1'-carboxylic acid, 4'-[(methylamino)carbonyl]-2-oxo-, phenylmethyl ester

Base Information

• Chemical Name: [1,4'-Bipiperidine]-1'-carboxylic acid, 4'-[(methylamino)carbonyl]-2-oxo-, phenylmethyl ester
• CAS No.: 166181-27-7
• Molecular Formula: C20H27N3O4
• Molecular Weight: 373.452
• Mol file: 166181-27-7.mol

Synonyms:

Chemical Property of [1,4'-Bipiperidine]-1'-carboxylic acid, 4'-[(methylamino)carbonyl]-2-oxo-, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1,4'-Bipiperidine]-1'-carboxylic acid, 4'-[(methylamino)carbonyl]-2-oxo-, phenylmethyl ester

There total 10 articles about [1,4'-Bipiperidine]-1'-carboxylic acid, 4'-[(methylamino)carbonyl]-2-oxo-, phenylmethyl ester 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: 80.0%

methylamine hydrochloride (593-51-1) + 1-benzyloxycarbonyl-4-carboxy-4-(2-oxopiperidino)piperidine (166180-94-5) → 1-benzyloxycarbonyl-4-methylaminocarbonyl-4-(2-oxopiperidino)piperidine (166181-27-7)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1021/jm020094i

Reference yield:

1-phenylmethyl-4-piperidone (3612-20-2) → 1-benzyloxycarbonyl-4-methylaminocarbonyl-4-(2-oxopiperidino)piperidine (166181-27-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 89 percent / H₂O; ethanol / 12 h / 60 °C

2: 66 percent / lithium hydroxide / H₂O / 40 h

3: 84 percent / thionyl chloride / Heating

4: 57 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

5: 87 percent / NaH / tetrahydrofuran

6: 99 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 760.05 Torr

7: 86 percent / Et₃N / CH₂Cl₂ / 1.5 h

8: 88 percent Turnov_. / 1 N aq. NaOH / tetrahydrofuran / 10 h / Heating

9: 80 percent / 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride; 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; lithium hydroxide; sodium hydroxide; thionyl chloride; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 20percent Pd(OH)2/C; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1021/jm020094i

Reference yield:

5-Chlorovaleroyl chloride (1575-61-7) → 1-benzyloxycarbonyl-4-methylaminocarbonyl-4-(2-oxopiperidino)piperidine (166181-27-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 57 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2: 87 percent / NaH / tetrahydrofuran

3: 99 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 760.05 Torr

4: 86 percent / Et₃N / CH₂Cl₂ / 1.5 h

5: 88 percent Turnov_. / 1 N aq. NaOH / tetrahydrofuran / 10 h / Heating

6: 80 percent / 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride; 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; sodium hydroxide; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 20percent Pd(OH)2/C; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm020094i

upstream raw materials:

methylamine hydrochloride

1-benzyloxycarbonyl-4-carboxy-4-(2-oxopiperidino)piperidine

1-phenylmethyl-4-piperidone

N-(Benzyloxycarbonyloxy)succinimide

Refernces

• 1、 -. "Lactam derivatives". . . Retrieved 2008/06/13.