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87120-72-7

87120-72-7

Identification

  • Product Name:1-Piperidinecarboxylicacid, 4-amino-, 1,1-dimethylethyl ester

  • CAS Number: 87120-72-7

  • EINECS:1312995-182-4

  • Molecular Weight:200.281

  • Molecular Formula: C10H20N2O2

  • HS Code:29339900

  • Mol File:87120-72-7.mol

Synonyms:1,1-Dimethylethyl4-amino-1-piperidinecarboxylate;1-(t-Butoxycarbonyl)-4-aminopiperidine;1-tert-Butoxycarbonyl-4-aminopiperidine;4-Amino-1-(tert-butyloxycarbonyl)piperidine;4-Amino-1-piperidinecarboxylic acid 1,1-dimethylethyl ester;4-Amino-1-tert-butoxycarbonylpiperidine;4-Amino-N-Boc-piperidine;4-Aminopiperidine-1-carboxylic acid tert-butyl ester;N-Boc-4-aminopiperidine;N-tert-Butoxycarbonyl-4-aminopiperidine;[N-(tert-Butoxycarbonyl)piperidin-4-yl]amine;tert-Butyl4-aminopiperidine-1-carboxylate;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn, IrritantXi

  • Hazard Codes:Xn,Xi

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH315 Causes skin irritation H318 Causes serious eye damage H335 May cause respiratory irritation

  • 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

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  • Manufacture/Brand:Usbiological
  • Product Description:4-Amino-1-Boc-piperidine
  • Packaging:25g
  • Price:$ 322
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  • Manufacture/Brand:TRC
  • Product Description:4-Amino-1-Boc-piperidine
  • Packaging:100g
  • Price:$ 690
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  • Manufacture/Brand:TRC
  • Product Description:4-Amino-1-Boc-piperidine
  • Packaging:5g
  • Price:$ 85
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  • Manufacture/Brand:TRC
  • Product Description:4-Amino-1-Boc-piperidine
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Amino-1-tert-butoxycarbonylpiperidine >97.0%(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Amino-1-tert-butoxycarbonylpiperidine >97.0%(T)
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  • Manufacture/Brand:SynChem
  • Product Description:4-Amino-piperidine-1-carboxylic acid tert-butyl ester 97+%
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  • Manufacture/Brand:SynChem
  • Product Description:4-Amino-piperidine-1-carboxylic acid tert-butyl ester 97+%
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  • Product Description:4-Amino-1-Boc-piperidine 97%
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Relevant articles and documentsAll total 53 Articles be found

sEH Inhibitor or pharmaceutically acceptable composition thereof as well as preparation method and application thereof

-

Paragraph 0117; 0119, (2021/09/21)

The invention provides sEH inhibitor or a pharmaceutically acceptable composition and a preparation method and application thereof, and belongs to the technical field of medicines. sEH Inhibitor or a pharmaceutically acceptable composition thereof according to the present invention is provided, and the sEH inhibitor has the structure shown I. sEH Inhibitor provided by the invention can stabilize an endogenous substance epoxy fatty acid with wide physiological activity, has a strong inhibition effect on human recombinant sEH, and can be used for regulating the generation of a plurality of pro-inflammatory cytokines. The invention relieves the stress of endoplasmic reticulum, prevents or reverses the dysfunction of endothelial dysfunction, stabilizes mitochondria function multiple action mechanisms to obviously relieve neuropathic pain, and can effectively avoid adverse reactions related to the target spot. Furthermore, the sEH inhibitor structure provided by the invention does not contain free carboxyl groups, can avoid adverse reactions such as gastrointestinal irritation caused by oral administration, and is small in adverse reaction, high in bioavailability, excellent in analgesic effect and small in administration amount.

Copper-catalysed amination of alkyl iodides enabled by halogen-atom transfer

Barthelemy, Anne-Laure,Douglas, James J.,Górski, Bartosz,Juliá, Fabio,Leonori, Daniele

, p. 623 - 630 (2021/07/25)

Despite the fact that nucleophilic displacement (SN2) of alkyl halides with nitrogen nucleophiles is one of the first reactions introduced in organic chemistry teaching, its practical utilization is largely limited to unhindered (primary) or ac

Direct Deamination of Primary Amines via Isodiazene Intermediates

Berger, Kathleen J.,Driscoll, Julia L.,Yuan, Mingbin,Dherange, Balu D.,Gutierrez, Osvaldo,Levin, Mark D.

supporting information, p. 17366 - 17373 (2021/11/04)

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.

PROCESSES AND COMPOUNDS FOR THE DECARBOXYLATIVE AMINATION OF REDOX-ACTIVE ESTERS WITH DIAZIRINES

-

Page/Page column 38, (2020/12/30)

The invention described herein relates generally to processes for the synthesis of amine-containing organic compounds. More specifically, described herein relates to processes for the decarboxylative amination of redox-active esters with diazirines and the products formed thereof. Compounds for use in the above processes are also described.

Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents

Chandrachud, Preeti P.,Wojtas, Lukasz,Lopchuk, Justin M.

, p. 21743 - 21750 (2021/01/11)

The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.

Process route upstream and downstream products

Process route

C<sub>18</sub>H<sub>24</sub>F<sub>3</sub>N<sub>3</sub>O<sub>2</sub>

C18H24F3N3O2

2,2,2-Trifluoroacetophenone
434-45-7

2,2,2-Trifluoroacetophenone

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
With chloro-trimethyl-silane; lithium chloride;
90%
tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate
211108-50-8

tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate

(3S,4R)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate
907544-20-1,577691-56-6

(3S,4R)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate

(3R,4R)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate
1260612-08-5,577691-56-6

(3R,4R)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
With sodium tetraborate decahydrate; pyridoxal 5'-phosphate; Codexis ATA-303 transaminase; isopropylamine; In water; dimethyl sulfoxide; at 20 - 45 ℃; for 24h; pH=10.5; pH-value; enantioselective reaction; Inert atmosphere; Enzymatic reaction;
94 % ee
tert-butyl 4-(hydroxyimino)piperidine-1-carboxylate
150008-24-5

tert-butyl 4-(hydroxyimino)piperidine-1-carboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
With hydrogen; Raney nickel; In ethanol; under 2585.81 Torr;
98%
With Raney nickel; In methanol; at 20 ℃; for 4h;
83%
With sodium; In propan-1-ol; at 98 ℃; for 2.5h;
74.9%
With hydrogen; 5% rhodium on activated aluminium oxide; In methanol; at 50 ℃;
4-benzylamino-piperidine-1-carboxylic acid tert-butyl ester
206273-87-2

4-benzylamino-piperidine-1-carboxylic acid tert-butyl ester

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
With hydrogen; palladium 10% on activated carbon; In ethanol; under 5320.36 Torr;
98%
With hydrogen; palladium 10% on activated carbon; In ethanol;
98%
With hydrogen; palladium on activated charcoal; In methanol;
1,1-dimethylethyl 4-[bis(phenylmethyl)amino]-1-piperidinecarboxylate
873088-90-5

1,1-dimethylethyl 4-[bis(phenylmethyl)amino]-1-piperidinecarboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
With hydrogen; palladium(II) hydroxide; In tetrahydrofuran; ethanol; at 23 ℃; for 6h; under 760.051 Torr; Inert atmosphere;
77%
4-aminopiperidine
13035-19-3

4-aminopiperidine

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
4-aminopiperidine; di-tert-butyl dicarbonate; In 4-methyl-2-pentanone; at 0 - 20 ℃; for 0.5h; Inert atmosphere; Reflux;
With water; In isopropyl alcohol; at 50 ℃;
85%
In dichloromethane; at 0 ℃; for 5h;
71.9%
4-aminopiperidine; With benzaldehyde; In toluene; for 3h; Heating / reflux;
di-tert-butyl dicarbonate; In toluene; at 20 ℃;
With triethylamine; In 1,4-dioxane; water;
With triethylamine; In 1,4-dioxane; water;
N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
N-tert-butyloxycarbonylpiperidin-4-one; With ammonium acetate; In methanol; at 20 ℃; for 0.166667h; Inert atmosphere;
With sodium cyanoborohydride; In methanol; at 60 ℃; for 16h; Inert atmosphere;
97%
N-tert-butyloxycarbonylpiperidin-4-one; With hydroxylamine hydrochloride; sodium carbonate; In water; at 23 ℃; for 14h;
With hydrogen; Raney Ni; In ethanol; for 3.5h; under 2585.81 Torr; Solid phase;
96%
In ammonia-saturated methanol; aluminum nickel;
95.4%
N-tert-butyloxycarbonylpiperidin-4-one; With titanium(IV) isopropylate; ammonia; In ethanol; at 25 ℃; for 6h;
With sodium tetrahydroborate; In ethanol; at 25 ℃; for 3h; Further stages.;
88%
With ammonia; hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;
84%
With titanium(IV) isopropylate; sodium tetrahydroborate; ammonia; In ethanol; at 20 - 30 ℃; for 4h; Inert atmosphere;
82%
With palladium on activated charcoal; ammonia; hydrogen; In methanol; at 20 ℃;
63%
N-tert-butyloxycarbonylpiperidin-4-one; With sodium tris(acetoxy)borohydride; acetic acid; dibenzylamine; In dichloromethane; at 0 - 20 ℃; for 16h;
With sodium hydroxide; In water;
With hydrogenchloride; sodium hydroxide; hydrogen; 20% palladium hydroxide on carbon; more than 3 stages;
49%
N-tert-butyloxycarbonylpiperidin-4-one; With titanium(IV) isopropylate; ammonia; In ethanol; at 20 ℃; for 6h;
With sodium tetrahydroborate; In ethanol; at 20 ℃; for 3h;
With ethanol; ammonia; water;
44%
With ammonia; hydrogen; palladium on activated charcoal; In methanol;
Multi-step reaction with 2 steps
1: pyridine; hydroxylamine hydrochloride / ethanol / 1 h / Reflux
2: Raney nickel / methanol / 4 h / 20 °C
With pyridine; hydroxylamine hydrochloride; In methanol; ethanol;
Multi-step reaction with 2 steps
1.1: acetic acid / dichloromethane / 3 h / 0 - 23 °C
1.2: 12 h / 23 °C
2.1: hydrogen / palladium(II) hydroxide / ethanol; tetrahydrofuran / 6 h / 23 °C / 760.05 Torr / Inert atmosphere
With hydrogen; palladium(II) hydroxide; acetic acid; In tetrahydrofuran; ethanol; dichloromethane;
Multi-step reaction with 2 steps
1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 3 h / 25 °C
2: hydrogen; palladium on activated charcoal / methanol / 16 h / 25 °C
With palladium on activated charcoal; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; In methanol; dichloromethane;
With palladium on activated charcoal; ammonia; hydrogen; In isopropyl alcohol; at 20 ℃; for 16h;
0.2 g
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; triethylamine / ethanol / 6 h / 0 - 20 °C / Heating / reflux
2: hydrogen / 5% rhodium on activated aluminium oxide / methanol / 50 °C
With hydroxylamine hydrochloride; hydrogen; triethylamine; 5% rhodium on activated aluminium oxide; In methanol; ethanol;
Multi-step reaction with 2 steps
1.1: triethylamine / methanol / 5 h / 65 °C
1.2: 48 h
2.1: hydrogen / palladium 10% on activated carbon / ethanol / 5320.36 Torr
With hydrogen; triethylamine; palladium 10% on activated carbon; In methanol; ethanol;
Multi-step reaction with 2 steps
1.1: triethylamine / methanol / 5 h / 65 °C
1.2: 48 h
2.1: hydrogen / palladium 10% on activated carbon / ethanol
With hydrogen; triethylamine; palladium 10% on activated carbon; In methanol; ethanol;
With pyridoxal 5'-phosphate; transaminase pQR2189; isopropylamine; In aq. phosphate buffer; dimethyl sulfoxide; at 35 ℃; for 18h; pH=7.5; Reagent/catalyst; Kinetics;
100 %Chromat.
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; potassium carbonate / ethanol / 1 h / 20 °C
2: sodium / propan-1-ol / 2.5 h / 98 °C
With hydroxylamine hydrochloride; sodium; potassium carbonate; In propan-1-ol; ethanol;
tert-butyl 4-[(2,4-dimethoxyphenyl)methylamino]piperidine-1-carboxylate

tert-butyl 4-[(2,4-dimethoxyphenyl)methylamino]piperidine-1-carboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
With palladium on activated charcoal; hydrogen; In methanol; at 25 ℃; for 16h;
81%
4-(benzylidene-amino)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester
1044183-50-7

4-(benzylidene-amino)-piperidine-1-carboxylic acid tert-butyl ester

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
With acetic acid; for 48h;
160 mg
With potassium hydrogensulfate; for 1.5h;
4.76 g
With sodium hydrogen sulfate; water; for 2h;
With potassium hydrogensulfate; water; In tert-butyl methyl ether; at 20 ℃; for 4h; Inert atmosphere;
6.0 g
tert-butyl 4-azidopiperidine-1-carboxylate
180695-80-1

tert-butyl 4-azidopiperidine-1-carboxylate

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

Conditions
Conditions Yield
With ammonium hydroxide; triphenylphosphine; In 1,4-dioxane; methanol; at 27 - 28 ℃; for 0.5h;
44%
With hydrogen; palladium on activated charcoal; In methanol; under 2068.59 Torr;
palladium-carbon; In methanol;
palladium-carbon; In methanol; hexane; ethyl acetate;

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