4-[(Chloro)(3-methoxyphenyl)methyl]-N,N-diethylbenzamide

Base Information

• Chemical Name: 4-[(Chloro)(3-methoxyphenyl)methyl]-N,N-diethylbenzamide
• CAS No.: 186094-10-0
• Molecular Formula: C19H22ClNO2
• Molecular Weight: 331.842
• DSSTox Substance ID: DTXSID70433942
• Mol file: 186094-10-0.mol

Synonyms:186094-10-0;4-[(CHLORO)(3-METHOXYPHENYL)METHYL]-N,N-DIETHYLBENZAMIDE;4-[chloro-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide;rac 4-(3'-Methoxy-alpha-chlorobenzyl)-N,N-diethylbenzamide;SCHEMBL1986972;DTXSID70433942;AKOS030255743;FT-0671201;4-[Chloro(3-methoxyphenyl)methyl]-N,N-diethylbenzamide;rac 4-(3'-Methoxy-?-chlorobenzyl)-N,N-diethylbenzamide;4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide;RAC-4-(3'-METHOXY-A-CHLOROBENZYL)-N,N-DIETHYLBENZAMIDE;rac 4-(3 inverted exclamation mark -Methoxy-|A-chlorobenzyl)-N,N-diethylbenzamide

Chemical Property of 4-[(Chloro)(3-methoxyphenyl)methyl]-N,N-diethylbenzamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 72-73°C
• Boiling Point: 483.53oC at 760 mmHg
• Flash Point: 246.231oC
• PSA: 29.54000
• Density: 1.131g/cm3
• LogP: 4.50540
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 331.1339066
• Heavy Atom Count: 23
• Complexity: 364

Purity/Quality:

99% ^*data from raw suppliers

rac4-(3’-Methoxy-α-chlorobenzyl)-N,N-diethylbenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1=CC=C(C=C1)C(C2=CC(=CC=C2)OC)Cl
• Uses: An intermediate of the δ opioid receptor-selective racemic agonist BW373U86 An intermediate of the δ opioid receptor-selective racemic agonist BW373U86.

Technology Process of 4-[(Chloro)(3-methoxyphenyl)methyl]-N,N-diethylbenzamide

There total 15 articles about 4-[(Chloro)(3-methoxyphenyl)methyl]-N,N-diethylbenzamide 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: 100.0%

(±)-4-[hydroxy-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide (186094-06-4) → 4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide (186094-10-0)

Guidance literature:

With hydrogenchloride; In chloroform;

DOI:10.1021/jm9903895

Reference yield:

4-(3-methoxybenzoyl)benzoic acid (156727-76-3) → 4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide (186094-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂ / benzene / 3 h / Heating

2: CHCl₃ / 4 h / Ambient temperature

3: 70 percent / NaBH₄ / ethanol; H₂O / 2 h / Heating

4: 11.16 g / 37percent aq. HCl / CHCl₃ / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; thionyl chloride; In ethanol; chloroform; water; benzene;

DOI:10.1021/jm960319n

Reference yield:

N,N-diethyl-4-(3-methoxybenzoyl)benzamide (156727-77-4) → 4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide (186094-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / NaBH₄ / ethanol; H₂O / 2 h / Heating

2: 11.16 g / 37percent aq. HCl / CHCl₃ / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; In ethanol; chloroform; water;

DOI:10.1021/jm960319n

upstream raw materials:

(±)-4-[hydroxy-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide

3-methoxyphenyl bromide

N,N-diethyl-4-formylbenzamide

(3-methoxyphenyl)magnesium bromide

Downstream raw materials:

(+)-4-[(αR)-α-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N,N-diethylbenzamide

SNC 79

SNC 83

SNC 67

Refernces

• 1、 -. "PHARMACEUTICAL COMPOUNDS". Page/Page column 49. . Retrieved 2011/07/06.
• 2、 Plobeck,Delorme,Wei,Yang,Zhou,Schwarz,Gawell,Gagnon,Pelcman,Schmidt,Yue,Walpole,Brown,Zhou,Labare,Payza,St-Ogne,Kamassah,Morin,Projean,Ducharme,Roberts. "New diarylmethylpiperazines as potent and selective nonpeptidic δ opioid receptor agonists with increased in vitro metabolic stability". . p. 3878 - 3894. Retrieved 2007/10/03.