2-(Piperidin-4-yl)-acetic acid ethyl ester

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2-(Piperidin-4-yl)-acetic acid ethyl ester Basic information
Uses
Product Name:2-(Piperidin-4-yl)-acetic acid ethyl ester
Synonyms:PIPERIDIN-4-YL-ACETIC ACID ETHYL ESTER;PIPERIDINE-4-YL-ACETIC ETHYL ESTER;(Piperidin-4-yl)acetic acid ethyl ester, 4-(2-Ethoxy-2-oxoethyl)piperidine;Ethyl 2-(4-piperidinyl)acetate hydrochloride;4-PIPERIDINE ACETIC ACID ETHYL ESTER;ETHYL 4-PIPERIDINEACETATE;ETHYL 2-(4-PIPERIDINYL)ACETATE;Ethyl 2-piperidin-4-ylacetate
CAS:59184-90-6
MF:C9H17NO2
MW:171.24
EINECS:
Product Categories:Piperidine
Mol File:59184-90-6.mol
2-(Piperidin-4-yl)-acetic acid ethyl ester Structure
2-(Piperidin-4-yl)-acetic acid ethyl ester Chemical Properties
Melting point 192 °C (decomp)
Boiling point 67°C/0.22mm
density 0.969±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
form liquid
pka10.41±0.10(Predicted)
CAS DataBase Reference59184-90-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
HazardClass IRRITANT
HS Code 2933399990
MSDS Information
2-(Piperidin-4-yl)-acetic acid ethyl ester Usage And Synthesis
UsesPiperidine derivatives have significant research value in the pharmaceutical field as drug intermediates. 4-Piperidine acetate methyl ester is also an important piperidine derivative drug intermediate, mainly used in the synthesis of drugs for various neurological diseases, such as convulsions, anti-epileptic drugs, and sedatives.
Synthesis
(1-BENZYLPIPERIDIN-4-YLIDENE)ACETIC ACID ETHYL ESTER

40110-55-2

2-(PIPERIDIN-4-YL)-ACETIC ACID ETHYL ESTER

59184-90-6

General procedure for the synthesis of ethyl 4-piperidineacetate from ethyl 2-(1-benzylpiperidin-4-ylidene)acetate: palladium/carbon catalyst (3.94 g) was added to a solution of 2-(1-benzylpiperidin-4-ylidene)ethyl acetate (24 g, 93 mmol) in ethyl acetate (300 mL). The reaction mixture was placed in an H-cubic hydrogenation reactor and the reaction conditions were set at 55 °C and 55 psi for 16 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford ethyl 4-piperidineacetate as a colorless oil (15 g, 90% yield). The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shifts δ: 4.10 (m, 2H), 3.03 (d, J = 16.4 Hz, 2H), 2.59 (t, J = 16.4 Hz, 2H), 2.19 (d, J = 9.6 Hz, 2H), 1.87 (m, 1H), 1.67 (d, J = 17.2 Hz, 2H ), 1.23 (t, J = 9.6Hz, 3H), 1.10 (m, 2H).

References[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 3065 - 3067
[2] Patent: WO2013/107336, 2013, A1. Location in patent: Page/Page column 17; 18
[3] Patent: US2015/80380, 2015, A1. Location in patent: Paragraph 0081; 0137; 0138; 0139
[4] Synthetic Communications, 2003, vol. 33, # 13, p. 2329 - 2338
2-(Piperidin-4-yl)-acetic acid ethyl ester Preparation Products And Raw materials
Raw materials(1-Benzylpiperidin-4-ylidene)acetic acid ethyl ester-->tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate-->Ethyl acetate-->Palladium-->Activated carbon-->Hydrogen
Tag:2-(Piperidin-4-yl)-acetic acid ethyl ester(59184-90-6) Related Product Information
Ethyl 4-piperidone-3-carboxylate hydrochloride (R)-1-Cbz-3-Piperidineacetic Acid Methyl Ester (R)-1-Boc-3-piperidineacetic acid methyl ester (S)-1-Cbz-3-Piperidineacetic Acid Methyl Ester (S)-3-Piperidineacetic acid methyl ester hydrochloride (S)-1-Boc-3-piperidineacetic acid methyl ester Methylphenidate hydrochloride 3-Methoxycarbonylmethyl-piperidine-1-carboxylic acid tert-butyl ester 2-(Piperidin-3-yl)-acetic acid ethyl ester 2-(Piperidin-3-yl)-acetic acid ethyl ester 2-(Piperidin-4-yl)-acetic acid ethyl ester Methyl 1-Boc-4-piperidineacetate Ethyl 2-piperidineacetate Methyl N-Cbz-3-piperidineacetate (2-OXO-PIPERIDIN-1-YL)-ACETIC ACID ETHYL ESTER (R)-(3-tert-Butoxycarbonylamino-piperidin-2-yl)-acetic acid ethyl ester Ethyl 3-quinuclidinecarboxylate Piperidin-4-yl-acetic acid tert-butyl ester