1-[1-[4-(1-acetylpiperidin-4-yl)oxy-2-methoxybenzoyl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one

Base Information

• Chemical Name: 1-[1-[4-(1-acetylpiperidin-4-yl)oxy-2-methoxybenzoyl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one
• CAS No.: 162042-44-6
• Molecular Formula: C₂₈H₃₃N₃O₆
• Molecular Weight: 507.587
• UNII: 98KJ8P9APP
• DSSTox Substance ID: DTXSID30426072
• Nikkaji Number: J713.193C
• Wikipedia: L-371,257
• Wikidata: Q6456065
• Pharos Ligand ID: RKQFV89SLNM6
• ChEMBL ID: CHEMBL24781
• Mol file: 162042-44-6.mol

Synonyms:1-(1-(4-((N-acetyl-4-piperidinyl)oxy)-2-methoxybenzoyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one;L 371257;L-371257

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Chemical Property of 1-[1-[4-(1-acetylpiperidin-4-yl)oxy-2-methoxybenzoyl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one

Chemical Property:

• Boiling Point: 728.9±60.0 °C(Predicted)
• PKA: 0.73±0.20(Predicted)
• PSA: 88.62000
• Density: 1.282±0.06 g/cm3(Predicted)
• LogP: 3.78710
• Storage Temp.: Store at RT
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 507.23693578
• Heavy Atom Count: 37
• Complexity: 823

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1CCC(CC1)OC2=CC(=C(C=C2)C(=O)N3CCC(CC3)N4C5=CC=CC=C5COC4=O)OC
• Uses: L-371,257 is a potent antagonist of oxytocin-induced contractions of the rat uterus in vitro and in vivo and has significant oral bioavailability in rats.

Technology Process of 1-[1-[4-(1-acetylpiperidin-4-yl)oxy-2-methoxybenzoyl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one

There total 13 articles about 1-[1-[4-(1-acetylpiperidin-4-yl)oxy-2-methoxybenzoyl]piperidin-4-yl]-4H-3,1-benzoxazin-2-one 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: 97.0%

acetic anhydride (108-24-7) + L 371209 hydrochloride → 1-(1-(4-((N-acetyl-4-piperidinyl)oxy)-2-methoxybenzoyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one (162042-44-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jm00023a002

Reference yield:

2-Aminobenzyl alcohol (5344-90-1) → 1-(1-(4-((N-acetyl-4-piperidinyl)oxy)-2-methoxybenzoyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one (162042-44-6)

Guidance literature:

Multi-step reaction with 7 steps

1: CH₃CO₂H / toluene / Heating

2: NaBH₃CN / tetrahydrofuran

3: 75 percent / iPr₂NEt / tetrahydrofuran

4: 99 percent / HCl (gas) / ethyl acetate

5: 90 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodimide hydrochloride, 1-hydroxybenzotriazole, iPr₂NEt / dimethylformamide

6: 99 percent / HCl (gas) / ethyl acetate

7: 97 percent / iPr₂NEt / CH₂Cl₂

With hydrogenchloride; sodium cyanoborohydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00023a002

Reference yield:

methyl 2,4-dihydroxybenzoate (2150-47-2) → 1-(1-(4-((N-acetyl-4-piperidinyl)oxy)-2-methoxybenzoyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one (162042-44-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran

2: 89 percent / NaH / dimethylformamide

3: 95 percent / aq. NaOH / methanol

4: 90 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodimide hydrochloride, 1-hydroxybenzotriazole, iPr₂NEt / dimethylformamide

5: 99 percent / HCl (gas) / ethyl acetate

6: 97 percent / iPr₂NEt / CH₂Cl₂

With hydrogenchloride; sodium hydroxide; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00023a002

upstream raw materials:

acetic anhydride

2-Aminobenzyl alcohol

methyl 2,4-dihydroxybenzoate

N-tert-butyloxycarbonylpiperidin-4-one

Refernces