4-[benzyl(ethoxycarbonylmethyl)amino]butyric acid ethyl ester
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
Conditions | Yield |
---|---|
Stage #1: 4-[benzyl(ethoxycarbonylmethyl)amino]butyric acid ethyl ester With sodium ethanolate In toluene at 20 - 85℃; for 3.5h; Large scale; Stage #2: With hydrogenchloride In water; toluene Large scale; | 94% |
Stage #1: 4-[benzyl(ethoxycarbonylmethyl)amino]butyric acid ethyl ester With sodium methylate In ethyl acetate for 4h; Reflux; Large scale; Stage #2: With water; sodium hydroxide pH=7 - 8; Large scale; Stage #3: With hydrogenchloride pH=1 - 2; Reagent/catalyst; Solvent; Large scale; | 8.6 kg |
ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 22℃; for 0.5h; Inert atmosphere; Large scale; | 76.8% |
4-bromoethylbutanoate
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / 1,4-dioxane / 22 h / Reflux; Large scale 2.1: sodium ethanolate / toluene / 3.5 h / 20 - 85 °C / Large scale 2.2: Large scale View Scheme |
ethyl 2-(benzylamino)acetate
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / 1,4-dioxane / 22 h / Reflux; Large scale 2.1: sodium ethanolate / toluene / 3.5 h / 20 - 85 °C / Large scale 2.2: Large scale View Scheme |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
ethyl 3-oxopiperidine-4-carboxylate
Conditions | Yield |
---|---|
In methanol; palladium dihydroxide | 100% |
With hydrogen; palladium dihydroxide In dichloromethane at 20℃; under 3750.3 Torr; for 24h; | 84% |
debenzylation; |
di-tert-butyl dicarbonate
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
ethyl 1-tert-butoxycarbonyl-3-oxopiperidine-4-carboxylate
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; triethylamine In methanol for 4h; Autoclave; | 100% |
With palladium 10% on activated carbon; hydrogen; sodium carbonate In ethanol at 50℃; under 28502.9 Torr; for 48h; Autoclave; | 100% |
With triethylamine; palladium-carbon In diethyl ether; ethanol | 94% |
di-tert-butyl dicarbonate
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
1-tert-butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate
Conditions | Yield |
---|---|
With Pd(OH)2/C; hydrogen; triethylamine In ethanol for 20h; | 100% |
formamidine acetic acid
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 2.5h; Inert atmosphere; Reflux; Large scale; | 100% |
guanidine hydrogen carbonate
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
2-amino-7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(4aH)-one
Conditions | Yield |
---|---|
With sodium ethanolate for 16h; Heating / reflux; | 99% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
benzyl bromide
(SR)-1,4-dibenzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; Large scale; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; Large scale; | 99% |
With NaH; sodium hydrogencarbonate In water; N,N-dimethyl-formamide |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
ethyl 3-hydroxypiperidine-4-carboxylate
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol at 20℃; under 760.051 Torr; for 48h; | 99% |
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 3.75 h / 0 - 20 °C 2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol / 14 h / 20 °C View Scheme |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
cyclopropylcarboxamidine hydrochloride
Conditions | Yield |
---|---|
With sodium methylate In methanol at 25℃; for 20h; Inert atmosphere; | 99% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In diethyl ether; water for 1h; | 96% |
With sodium ethanolate In ethanol | |
With sodium hydrogencarbonate In ethyl acetate for 2h; | |
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 0.5h; | 0.87 g |
guanidine hydrochloride
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
2-amino-7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(4aH)-one
Conditions | Yield |
---|---|
With sodium methylate In methanol at 100℃; | 96% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
Conditions | Yield |
---|---|
With 5% Pd(II)/C(eggshell); hydrogen In ethanol at 20℃; under 3750.38 Torr; for 4h; | 95% |
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 40℃; for 8h; | 91.4% |
With hydrogen; palladium 10% on activated carbon In ethanol at 50℃; for 4h; | 84% |
acetamidine hydrochloride
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
7-benzyl-2-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(3H)-one
Conditions | Yield |
---|---|
With sodium methylate In methanol at 25℃; for 20h; Inert atmosphere; | 95% |
With sodium ethanolate In ethanol for 16h; Product distribution / selectivity; Heating / reflux; | 77% |
With sodium ethanolate In ethanol; water; acetic acid | 17.1 g (95%) |
Stage #1: acetamidine hydrochloride; ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride With sodium ethanolate In ethanol at 100℃; for 15h; Stage #2: With hydrogenchloride In water pH=11; Product distribution / selectivity; |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
ethyl bromoacetate
Conditions | Yield |
---|---|
Stage #1: ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride With potassium tert-butylate In tetrahydrofuran at 6 - 29℃; for 4h; Large scale; Stage #2: ethyl bromoacetate In tetrahydrofuran at 10 - 20℃; for 29h; Large scale; | 94% |
di-tert-butyl dicarbonate
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
1-tert-butyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate
Conditions | Yield |
---|---|
With hydrogen; triethylamine; palladium(II) hydroxide/carbon In ethanol under 3102.97 Torr; for 5h; | 93% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
5-amino-3-methylthio-1,2,4-triazole
A
8-benzyl-2-methylthio-6,7,8,9-tetrahydropyrido<3,4-d>-1,2,4-triazolo<1,5-a>pyrimidin-5(10H)-one
Conditions | Yield |
---|---|
In acetic acid for 6.5h; Heating; | A 91% B 2% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
1,1-dimethylguanidine dihydrogensulfate
Conditions | Yield |
---|---|
With sodium methylate In methanol at 25℃; for 20h; Inert atmosphere; | 90% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
thiourea
methyl iodide
7-benzyl-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4(4aH)-one
Conditions | Yield |
---|---|
Stage #1: ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride; thiourea With sodium methylate In methanol at 100℃; Stage #2: methyl iodide In methanol at 20℃; for 1h; | 88% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
allyl bromide
Conditions | Yield |
---|---|
Stage #1: ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 84% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
urea
7-benzyl-5,6,7,8-tetrahydropyridine[3,4-d]pyrimidine-2,4-diol
Conditions | Yield |
---|---|
With sodium In ethanol at 75℃; for 36h; | 83.2% |
With ethanol; sodium at 75℃; for 36h; | 83.2% |
With ethanol; sodium at 90℃; for 12h; | 62% |
With ethanol; sodium at 80℃; for 20h; | 62% |
With sodium methylate In methanol; ethanol for 4h; Reflux; |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
6-benzyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-ol
Conditions | Yield |
---|---|
With hydrazine hydrate; triethylamine In ethanol at 80℃; for 1.5h; | 83% |
With hydrazine at 20℃; for 48h; |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
5-amino-3-methylthio-1,2,4-triazole
Conditions | Yield |
---|---|
With acetic acid for 8h; Condensation; Heating; | 81% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
urea
7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione
Conditions | Yield |
---|---|
With sodium methylate In ethanol for 17h; Heating / reflux; | 80% |
With sodium methylate In methanol for 18h; Reflux; Inert atmosphere; | 58.3% |
With sodium methylate In methanol at 0℃; for 20h; Reflux; Inert atmosphere; |
benzamidine monohydrochloride
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
C20H19N3O
Conditions | Yield |
---|---|
With sodium methylate In methanol; ethanol at 0℃; Heating / reflux; | 80% |
2-methylisothiourea sulphate
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20℃; for 12h; | 80% |
formamidine acetic acid
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one
Conditions | Yield |
---|---|
With sodium methylate In methanol at 25℃; for 20h; Inert atmosphere; | 79% |
Stage #1: formamidine acetic acid; ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride With sodium methylate In methanol at 25℃; for 20h; Stage #2: With acetic acid In methanol; water at 0 - 25℃; | 79% |
With sodium methylate In methanol at 20℃; for 20h; | 70% |
Stage #1: formamidine acetic acid; ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride With sodium methylate In methanol at 20℃; for 20h; Stage #2: With acetic acid In methanol; water at 0 - 20℃; for 1h; | 70% |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
trifluoroacetamidine
7-benzyl-2-(trifluoromethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-ol
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 20 - 80℃; for 17.25h; | 78% |
With ethanol; sodium at 20 - 80℃; for 17h; Inert atmosphere; | 78% |
With sodium ethanolate In ethanol at 20℃; for 31.25h; | |
Stage #1: ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride; trifluoroacetamidine With sodium ethanolate at 20℃; for 1.25h; Stage #2: for 30h; Heating / reflux; | |
With sodium ethanolate In ethanol for 31.25h; Heating / reflux; |
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
ethyl 2-amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
Conditions | Yield |
---|---|
With ammonium acetate In ethanol at 20℃; for 1h; | 75% |
With ammonium acetate In ethanol at 20℃; for 1h; | |
With ammonium acetate In ethanol at 20℃; for 3h; | 29.2 g |
With ammonium acetate In ethanol at 20℃; for 3h; | 29.2 g |
5-amino-3-morpholino-1H-1,2,4-triazole
ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride
A
8-benzyl-2-morpholino-6,7,8,9-tetrahydropyrido<3,4-d>-1,2,4-triazolo<1,5-a>pyrimidin-5(10H)-one
Conditions | Yield |
---|---|
In acetic acid for 7h; Heating; | A 72% B 3% |
The Ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride, with the CAS registry number 52763-21-0 and EINECS registry number 258-162-5, has the systematic name of ethyl 1-benzyl-3-oxo-piperidine-4-carboxylate hydrochloride. It is a kind of white to brown crystalline powder, and belongs to the following product categories: Piperidines, Piperidones, Piperazines. And the molecular formula of this chemical is C15H20ClNO3.
The physical properties of Ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride are as followings: (1)H-Bond Donor: 1; (2)H-Bond Acceptor: 4; (3)Rotatable Bond Count: 5; (4)Tautomer Count: 5; (5)Exact Mass: 297.113171; (6)MonoIsotopic Mass: 297.113171; (7)Topological Polar Surface Area: 46.6; (8)Heavy Atom Count: 20; (9)Formal Charge: 0; (10)Complexity: 323; (11)Isotope Atom Count: 0; (12)Defined Atom StereoCenter Count: 0; (13)Undefined Atom StereoCenter Count: 1; (14)Defined Bond StereoCenter Count: 0; (15)Undefined Bond StereoCenter Count: 0; (16)Covalently-Bonded Unit Count: 2.
Uses of Ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride: It can react with 5-methylamino-3-methylthio-1,2,4-triazole to produce 6-benzyl-10-methyl-2-methylthio-5,6,7,8-tetrahydropyrido[4,3-e]-1,2,4-triazolo[1,5-a]pyrimidin-9(10H)-one. This reaction will need reagent acetic acid. The reaction time is 6 hours with heating, and the yield is about 62%.
You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: CCOC(=O)C1CCN(CC1=O)Cc2ccccc2.Cl
(2)InChI: InChI=1/C15H19NO3.ClH/c1-2-19-15(18)13-8-9-16(11-14(13)17)10-12-6-4-3-5-7-12;/h3-7,13H,2,8-11H2,1H3;1H
(3)InChIKey: UQOMEAWPKSISII-UHFFFAOYAM
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