N-[2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide

Base Information

• Chemical Name: N-[2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide
• CAS No.: 272788-07-5
• Molecular Formula: C16H23NO3
• Molecular Weight: 277.364
• DSSTox Substance ID: DTXSID00573582
• Mol file: 272788-07-5.mol

Synonyms:272788-07-5;N-FORMYL-1-(2-AMINO-1-(4-METHOXYPHENYL)ETHYL)CYCLOHEXANOL;N-[2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide;SCHEMBL12187989;DTXSID00573582

Chemical Property of N-[2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide

Chemical Property:

• PSA: 62.05000
• LogP: 3.06030
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 277.16779360
• Heavy Atom Count: 20
• Complexity: 294

Purity/Quality:

NLT 98% ^*data from raw suppliers

N-Formyl-1-(2-amino-1-(4-methoxyphenyl)ethyl)cyclohexanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(CNC=O)C2(CCCCC2)O
• Uses: An intermediate in the synthesis of N,O-Didesmethylvenlafaxine, a metabolite of Venlafaxine An intermediate in the synthesis of N,O-Didesmethylvenlafaxine, a metabolite of Venlafaxine.

Technology Process of N-[2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide

There total 4 articles about N-[2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide 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: 99.0%

formic acid (64-18-6) + N,N-didesmethylvenlafaxine (93413-77-5,272788-06-4,273720-73-3,149289-31-6) → N-[2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide (272788-07-5)

Guidance literature:

In toluene; for 5h; Reflux;

DOI:10.1080/00397910903162767

Reference yield:

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol (93413-76-4,131801-69-9) → N-[2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide (272788-07-5)

Guidance literature:

Multi-step reaction with 2 steps

1: cobalt(II) chloride; sodium tetrahydroborate / methanol / 2 h / 20 - 35 °C

2: toluene / 4 h / Reflux

With sodium tetrahydroborate; cobalt(II) chloride; In methanol; toluene;

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → N-[2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide (272788-07-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 - -65 °C

1.2: 2 h / -78 - -65 °C

2.1: cobalt(II) chloride; sodium tetrahydroborate / methanol / 2 h / 20 - 35 °C

3.1: toluene / 4 h / Reflux

With sodium tetrahydroborate; cobalt(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; toluene;

upstream raw materials:

formic acid

N,N-didesmethylvenlafaxine

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol

cyclohexanone

Downstream raw materials:

N-Desmethylvenlafaxine

Refernces

• 1、 Saravanan, Mohanarangam,Kumar, Karra Suresh,Reddy, Padi Pratap,Satyanarayana, Bollikonda. "Impurity profile study of venlafaxine hydrochloride, an antipsychotic drug substance". experimental part. p. 1880 - 1886. Retrieved 2010/09/07.