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Cas Database

1863-07-6

1863-07-6

Identification

  • Product Name:fentanyl citrate

  • CAS Number: 1863-07-6

  • EINECS:

  • Molecular Weight:528.602

  • Molecular Formula: C6H8O7*C22H28N2O

  • HS Code:

  • Mol File:1863-07-6.mol

Synonyms:

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Relevant articles and documentsAll total 2 Articles be found

An efficient, optimized synthesis of fentanyl and related analogs

Valdez, Carlos A.,Leif, Roald N.,Mayer, Brian P.

, (2014)

The alternate and optimized syntheses of the parent opioid fentanyl and its analogs are described. The routes presented exhibit high-yielding transformations leading to these powerful analgesics after optimization studies were carried out for each synthetic step. The general three-step strategy produced a panel of four fentanyls in excellent yields (73-78%) along with their more commonly encountered hydrochloride and citric acid salts. The following strategy offers the opportunity for the gram-scale, efficient production of this interesting class of opioid alkaloids.

SUBSTITUTED 4-AMINO-PIPERIDINES

-

Page/Page column 20, (2010/02/17)

The present invention relates to new substituted 4-amino-piperidine opioid receptor modulators, pharmaceutical compositions thereof, and methods of use thereof

Process route upstream and downstream products

Process route

N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide
437-38-7

N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide

fentanyl citrate
1863-07-6,990-73-8

fentanyl citrate

Conditions
Conditions Yield
In methanol; at 20 ℃; for 2h;
95%
In ethanol; at 20 ℃; for 20h; Reflux;
62%
4-piperidone hydrochloride
41979-39-9

4-piperidone hydrochloride

fentanyl citrate
1863-07-6,990-73-8

fentanyl citrate

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: caesium carbonate / acetonitrile / 5 h / 80 °C
2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C / Cooling with ice
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
4: methanol / 2 h / 20 °C
With sodium tris(acetoxy)borohydride; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile;
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

fentanyl citrate
1863-07-6,990-73-8

fentanyl citrate

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: caesium carbonate / acetonitrile / 5 h / 80 °C
2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C / Cooling with ice
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
4: methanol / 2 h / 20 °C
With sodium tris(acetoxy)borohydride; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile;
1-(2-phenylethyl)-4-piperidinone
39742-60-4

1-(2-phenylethyl)-4-piperidinone

fentanyl citrate
1863-07-6,990-73-8

fentanyl citrate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C / Cooling with ice
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
3: methanol / 2 h / 20 °C
With sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

(1-Phenethyl-piperidin-4-yl)-phenyl-amine

fentanyl citrate
1863-07-6,990-73-8

fentanyl citrate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
2: methanol / 2 h / 20 °C
With N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
fentanyl citrate
1863-07-6,990-73-8

fentanyl citrate

Conditions
Conditions Yield
1-(β-Phenylethyl)-4-(N-propionyl)-anilino-piperidin-hydrochlorid, 1.) verd. wss. NaOH (zur entspr. Base), 2.) A., Zitronensaeure;
fentanyl citrate
1863-07-6,990-73-8

fentanyl citrate

N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide
437-38-7

N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide

Conditions
Conditions Yield
With sodium hydrogencarbonate; In water;
94%

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