4-(Methoxymethyl)-N-phenyl-1-(2-(thiophen-2-yl)ethyl)piperidin-4-amine

Base Information

• Chemical Name: 4-(Methoxymethyl)-N-phenyl-1-(2-(thiophen-2-yl)ethyl)piperidin-4-amine
• CAS No.: 72996-73-7
• Molecular Formula: C₁₉H₂₆N₂OS
• Molecular Weight: 330.494
• European Community (EC) Number: 680-255-8
• UNII: C9PAV4BVF4
• DSSTox Substance ID: DTXSID901165428
• Mol file: 72996-73-7.mol

Synonyms:C9PAV4BVF4;72996-73-7;UNII-C9PAV4BVF4;Sufentanil impurity E [EP];4-(Methoxymethyl)-N-phenyl-1-(2-(thiophen-2-yl)ethyl)piperidin-4-amine;Sufentanil citrate impurity E [EP];4-(Methoxymethyl)-N-phenyl-1-(2-(2-thienyl)ethyl)-4-piperidinamine;4-(Methoxymethyl)-N-phenyl-1-(2-(thien-2-yl)ethyl)piperidin-4-amine;4-Piperidinamine, 4-(methoxymethyl)-N-phenyl-1-(2-(2-thienyl)ethyl)-;4-(Methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]-4-piperidinamine;SCHEMBL781667;UBUDUWLTRRWLSI-UHFFFAOYSA-N;DTXSID901165428;SUFENTANIL IMPURITY E [EP IMPURITY];SUFENTANIL CITRATE IMPURITY E [EP IMPURITY];N-(2-Thien-2-ylethyl)-4-(phenylamino)-4-(methoxymethyl)piperidine;4-(Methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]-4-piperidinamine (DO NOT DISPENSE/NOT FOR EXTERNAL SALES)

Chemical Property of 4-(Methoxymethyl)-N-phenyl-1-(2-(thiophen-2-yl)ethyl)piperidin-4-amine

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 330.17658463
• Heavy Atom Count: 23
• Complexity: 338

Purity/Quality:

>95% ^*data from raw suppliers

4-(Methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]-4-piperidinamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COCC1(CCN(CC1)CCC2=CC=CS2)NC3=CC=CC=C3
• Uses: 4-(Methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]-4-piperidinamine is an impurity of Sufentanil (S699040), a potent derivative of Fentanyl. Analgesic (narcotic), and a controlled substance (opiate).

Technology Process of 4-(Methoxymethyl)-N-phenyl-1-(2-(thiophen-2-yl)ethyl)piperidin-4-amine

There total 8 articles about 4-(Methoxymethyl)-N-phenyl-1-(2-(thiophen-2-yl)ethyl)piperidin-4-amine 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: 85.93%

(4-(phenylamino)-1-(2-(thiophen-2-yl)ethyl)piperidin-4-yl)methanol + methyl iodide (74-88-4) → 4-(Methoxymethyl)-N-phenyl-1-<2-(2-thienyl)ethyl>-4-piperidinamine (72996-73-7)

Guidance literature:

(4-(phenylamino)-1-(2-(thiophen-2-yl)ethyl)piperidin-4-yl)methanol; With sodium hydride; tert-butyl alcohol; In diethylene glycol dimethyl ether; mineral oil; at 70 ℃; for 2h; Inert atmosphere;

methyl iodide; In diethylene glycol dimethyl ether; mineral oil; at 5 - 6 ℃; for 17.5h;

Reference yield: 72.1%

4-(methoxymethyl)-N-phenylpiperidin-4-amine + 2-(thiophen-2-yl)ethyl methanesulfonate (61380-07-2) → 4-(Methoxymethyl)-N-phenyl-1-<2-(2-thienyl)ethyl>-4-piperidinamine (72996-73-7)

Guidance literature:

With triethylamine; potassium iodide; In acetonitrile; Inert atmosphere; Reflux;

Reference yield:

aniline (62-53-3) → 4-(Methoxymethyl)-N-phenyl-1-<2-(2-thienyl)ethyl>-4-piperidinamine (72996-73-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide / tetrahydrofuran; chloroform / 13 h / 0 - 20 °C

2.1: sodium hydroxide / dimethyl sulfoxide / 1 h / 20 °C

2.2: 12 h / 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 10 °C

4.1: n-butyllithium / toluene; diethyl ether / 1 h / 20 °C

4.2: 3 h / 20 °C

5.1: hydrogenchloride / ethyl acetate; water / 1 h

6.1: triethylamine; potassium iodide / acetonitrile / Inert atmosphere; Reflux

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; triethylamine; potassium iodide; sodium hydroxide; In tetrahydrofuran; diethyl ether; chloroform; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile;

upstream raw materials:

methyl iodide

2-(thiophen-2-yl)ethyl methanesulfonate

aniline

N-tert-butyloxycarbonylpiperidin-4-one

Refernces

• 1、 -. "Process for the Preparation of Sufentanil Base and Related Compounds". Page/Page column 7-8. . Retrieved 2012/04/04.