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Cas Database

21409-26-7

21409-26-7

Identification

  • Product Name:N-Phenyl-1-(2-phenethyl)piperidin-4-amine

  • CAS Number: 21409-26-7

  • EINECS:

  • Molecular Weight:280.413

  • Molecular Formula: C19H24N2

  • HS Code:29333990

  • Mol File:21409-26-7.mol

Synonyms:Piperidine,4-anilino-1-phenethyl- (8CI);1-Phenethyl-N-phenylpiperidin-4-amine;4-Anilino-1-(2-phenethyl)piperidine;4-Anilino-1-(b-phenethyl)piperidine;4-Anilino-1-phenethylpiperidine;Depropionylfentanyl;N-[1-(2-Phenylethyl)-4-piperidinyl]aniline;4-Piperidinamine,N-phenyl-1-(2-phenylethyl)-;

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Relevant articles and documentsAll total 19 Articles be found

-

Janicki et al.

, p. 451,452 (1968)

-

Evaluation of agonistic activity of fluorinated and nonfluorinated fentanyl analogs on μ-opioid receptor using a cell-based assay system

Kanamori, Tatsuyuki,Okada, Yuki,Segawa, Hiroki,Yamamuro, Tadashi,Kuwayama, Kenji,Tsujikawa, Kenji,Iwata, Yuko Togawa

, p. 159 - 161 (2021/02/09)

The agonistic activity of fluorinated and nonfluorinated fentanyl analogs on μ-opioid receptor was investigated using a cell-based assay system. Based on the activity, fentanyl analogs were ranked as follows: fentanyl>isobutyrylfentanyl≈butyrylfentanyl≈methoxyacetylfentanyl>acetylfentanyl. However, among the fentanyl analogs fluorinated on the Nphenyl ring, 2-fluoro analogs and 3-fluoro analogs showed the strongest and weakest activities, respectively. These results suggest that the 2-fluorinated isomers of fentanyl analogs are more likely to cause poisoning.

ADJUVANTED CONJUGATE OPIOID VACCINE

-

, (2021/12/08)

The adjuvanted conjugate opioid vaccine described herein is a conjugate of a protein carrier and at least one opioid backbone component or hapten conjugated thereto, admixed with at least one adjuvant. Anti-opioid effects are demonstrated after administration of a vaccine made up of the CRM197 protein carrier linked to a FEN backbone, combined with adjuvants such as dmLT or LTA1.

Chemoselective Reductive Aminations in Aqueous Nanoreactors Using Parts per Million Level Pd/C Catalysis

Casotti, Gianluca,Gao, Eugene S.,Jin, Henry S.,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.

supporting information, (2020/09/09)

Condensation in recyclable water between aldehydes or ketones and amines occurs smoothly within the hydrophobic cores of nanomicelles, resulting in imine formation that is subject to subsequent reduction leading, overall, to reductive amination. This micellar technology enables the synthesis of several types of pharmaceuticals, a new procedure that relies on only 2000 ppm (0.20 mol %) palladium from commercially available Pd/C. A broad range of substrates can be used under mild conditions, leading to high chemical yields of the desired secondary and tertiary amines.

Fentanyl family at the mu-opioid receptor: Uniform assessment of binding and computational analysis

Lipiński, Piotr F.J.,Kosson, Piotr,Matalińska, Joanna,Roszkowski, Piotr,Czarnocki, Zbigniew,Jarończyk, Ma?gorzata,Misicka, Aleksandra,Dobrowolski, Jan Cz.,Sadlej, Joanna

, (2019/02/26)

Interactions of 21 fentanyl derivatives with μ-opioid receptor (μOR) were studied using experimental and theoretical methods. Their binding to μOR was assessed with radioligand competitive binding assay. A uniform set of binding affinity data contains val

Metabolism of butyrylfentanyl in fresh human hepatocytes: Chemical synthesis of authentic metabolite standards for definitive identification

Kanamori, Tatsuyuki,Iwata, Yuko Togawa,Segawa, Hiroki,Yamamuro, Tadashi,Kuwayama, Kenji,Tsujikawa, Kenji,Inoue, Hiroyuki

, p. 623 - 630 (2019/05/08)

The metabolism of butyrylfentanyl, a new designer drug, was investigated using fresh human hepatocytes isolated from a liver-humanized mouse model. In the culture medium of hepatocytes incubated with butyrylfentanyl, the desphenethylated metabolite (nor-butyrylfentanyl), w-hydroxy-butyrylfentanyl, (w-1)-hydroxy-butyrylfentanyl, 4′-hydroxy-butyrylfentanyl, β-hydroxy-butyrylfentanyl, 4′-hydroxy-3′- methoxy-butyrylfentanyl, and w-carboxy-fentanyl were identified as the metabolites of butyrylfentanyl. Each metabolite was definitively identified by comparing the analytical data with those of authentic standards. The amount of the main metabolite, nor-butyrylfentanyl, reached 37% of the initial amount of butyrylfentanyl at 48 h. W-Hydroxy-butyrylfentanyl and (w-1)-hydroxy-butyrylfentanyl, formed by hydroxylation at the Nbutyryl group of butyrylfentanyl, were the second and third largest metabolites, respectively. The majority of 4′-hydroxy-butyrylfentanyl and 4′-hydroxy-3′-methoxy-butyrylfentanyl was considered to be conjugated. CYP reaction phenotyping for butyrylfentanyl using human liver microsomes and various anti-CYP antibodies revealed that CYP3A4 was involved in the formation of nor-butyrylfentanyl, (w-1)-hydroxybutyrylfentanyl, and β-hydroxy-butyrylfentanyl. In contrast, CYP2D6 was involved in the formation of w-hydroxy-butyrylfentanyl.

Process route upstream and downstream products

Process route

1-(2-phenylethyl)-4-piperidinone
39742-60-4

1-(2-phenylethyl)-4-piperidinone

aniline
62-53-3

aniline

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20 ℃; for 2h; Reagent/catalyst; Cooling with ice;
91%
With hydrogen; acetic acid; In ethanol; at 60 ℃; for 5h; under 3000.3 Torr; Temperature; Pressure; Solvent; Autoclave; Molecular sieve;
90.2%
1-(2-phenylethyl)-4-piperidinone; aniline; With acetic acid; In dichloromethane;
With sodium tris(acetoxy)borohydride; In dichloromethane; at 0 ℃;
89%
1-(2-phenylethyl)-4-piperidinone; aniline; With acetic acid; In toluene; at 50 - 60 ℃; for 0.25h;
With sodium tris(acetoxy)borohydride; In toluene; at 0 - 20 ℃; for 20h;
With sodium hydroxide; water; In toluene; for 0.5h;
87.6%
With triethylsilane; palladium on carbon; TPGS-750-M; acetic acid; In water; at 55 ℃; for 12h;
87%
1-(2-phenylethyl)-4-piperidinone; aniline; With acetic acid; In dichloromethane; at 30 ℃; for 0.166667h;
With sodium tetrahydroborate; sodium tris(acetoxy)borohydride; In dichloromethane; at 30 ℃; for 4h;
76.5%
With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 0 - 20 ℃; for 16h;
76%
1-(2-phenylethyl)-4-piperidinone; aniline; With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 0 - 20 ℃;
With sodium hydroxide; In dichloromethane; water; at 0 ℃; pH=9;
62%
With sodium tetrahydroborate; toluene-4-sulfonic acid; Yield given. Multistep reaction; 1) toluene, 22 h, reflux, 2) ethanol, rt, 3 h;
With sodium tetrahydroborate; molecular sieve; Yield given. Multistep reaction; 1) benzene, reflux, 20 h; 2) EtOH, room temp., 5 h;
With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20 ℃; for 24h;
With sodium tetrahydroborate; Molecular sieve;
With sodium tetrahydroborate; Molecular sieve;
With sodium tris(acetoxy)borohydride;
N-(1-phenethylpiperidin-4-ylidene)aniline
57958-48-2

N-(1-phenethylpiperidin-4-ylidene)aniline

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
With sodium tetrahydroborate; In methanol;
75.1%
With sodium tetrahydroborate; In methanol;
With sodium tetrahydroborate;
4-piperidone hydrochloride
41979-39-9

4-piperidone hydrochloride

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: triethylamine / CH2Cl2 / 0.5 h / 20 °C
1.2: sodium triacetoxyborohydride / CH2Cl2 / 24 h / 20 °C
2.1: sodium triacetoxyborohydride; acetic acid / CH2Cl2 / 24 h / 20 °C
With sodium tris(acetoxy)borohydride; acetic acid; triethylamine; In dichloromethane;
Multi-step reaction with 2 steps
1: caesium carbonate / acetonitrile / 5 h / 80 °C
2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C / Cooling with ice
With sodium tris(acetoxy)borohydride; caesium carbonate; acetic acid; In dichloromethane; acetonitrile;
Multi-step reaction with 2 steps
1.1: acetic acid; zinc / 24 h / 20 - 70 °C
1.2: Cooling with ice
2.1: sodium hydroxide / 120 °C
With acetic acid; sodium hydroxide; zinc;
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 5 h / 80 °C
2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 0 - 20 °C
With sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; In dichloromethane; acetonitrile;
aniline
62-53-3

aniline

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: acetic acid; zinc / 24 h / 20 - 70 °C
1.2: Cooling with ice
2.1: sodium hydroxide / 120 °C
With acetic acid; sodium hydroxide; zinc;
Multi-step reaction with 2 steps
1: acetic acid / toluene
2: sodium tetrahydroborate / methanol
With sodium tetrahydroborate; acetic acid; In methanol; toluene;
Multi-step reaction with 2 steps
1: Molecular sieve
2: sodium tetrahydroborate
With sodium tetrahydroborate;
1-(2-phenylethyl)-4-piperidinone
39742-60-4

1-(2-phenylethyl)-4-piperidinone

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: acetic acid / toluene
2: sodium tetrahydroborate / methanol
With sodium tetrahydroborate; acetic acid; In methanol; toluene;
Multi-step reaction with 2 steps
1: Molecular sieve
2: sodium tetrahydroborate
With sodium tetrahydroborate;
phenyl-piperidin-4-yl-amine
23056-29-3

phenyl-piperidin-4-yl-amine

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
With sodium hydroxide; at 120 ℃; Product distribution / selectivity;
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: caesium carbonate / acetonitrile / 5 h / 80 °C
2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C / Cooling with ice
With sodium tris(acetoxy)borohydride; caesium carbonate; acetic acid; In dichloromethane; acetonitrile;
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 5 h / 80 °C
2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 0 - 20 °C
With sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; In dichloromethane; acetonitrile;
phenylacetaldehyde
122-78-1

phenylacetaldehyde

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: triethylamine / CH2Cl2 / 0.5 h / 20 °C
1.2: sodium triacetoxyborohydride / CH2Cl2 / 24 h / 20 °C
2.1: sodium triacetoxyborohydride; acetic acid / CH2Cl2 / 24 h / 20 °C
With sodium tris(acetoxy)borohydride; acetic acid; triethylamine; In dichloromethane;
phenethylamine
64-04-0

phenethylamine

(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: methanol / 8.5 h / Cooling with ice; Reflux
2: sodium / methanol; toluene / 3.75 h / Reflux
3: acetic acid; hydrogen / ethanol / 5 h / 60 °C / 3000.3 Torr / Autoclave; Molecular sieve
With hydrogen; sodium; acetic acid; In methanol; ethanol; toluene;
(1-Phenethyl-piperidin-4-yl)-phenyl-amine
21409-26-7

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

Conditions
Conditions Yield
Suspension von LiAlH4 in Ae., 1.) 1-(β-Phenylethyl)-4-phenylimino-piperidin (XVIII) in Ae. (tropfenweise), 2.) Δ (S. 133);
XVIIII in Me., 1.) NaBH4 (tropfenweise), 2.) Δ (S. 133);
1-(2-Phenylethyl)-4-piperidon, 1.) Anilin, 2.) Na/A./Eisessig;
Me., 1.) Na, 2.) N-Phenyl-1-(β-phenylethyl)-piperidin-4-imin, 3.) NaBH4 (portionsweise), 4.) Kochen;
Fentanyl, Hydrolyse m. wss. HCl;
N-(β-Phenethyl)-4-anilinopyridinbromid, NaBH4;

Global suppliers and manufacturers

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