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7516-33-8

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7516-33-8 Usage

General Description

4-Piperidinone, 1,2,5-trimethyl- is a chemical compound with the molecular formula C9H17NO. It is a cyclic amide and a derivative of piperidinone, which is commonly used in the synthesis of pharmaceuticals and agrochemicals. This chemical is used as a building block in organic synthesis and as a reagent in various chemical reactions. It is a colorless liquid with a characteristic odor and is soluble in various organic solvents. It is important to handle 4-Piperidinone, 1,2,5-trimethyl- with care and follow proper safety precautions as it can be hazardous if not handled properly.

Check Digit Verification of cas no

The CAS Registry Mumber 7516-33-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,5,1 and 6 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 7516-33:
(6*7)+(5*5)+(4*1)+(3*6)+(2*3)+(1*3)=98
98 % 10 = 8
So 7516-33-8 is a valid CAS Registry Number.

7516-33-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2,5-trimethylpiperidin-4-one

1.2 Other means of identification

Product number -
Other names 1,2,5-trimethyl-4-ketopiperidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7516-33-8 SDS

7516-33-8Synthetic route

5-methoxy-2-methyl-1-hexen-3-one
13058-36-1

5-methoxy-2-methyl-1-hexen-3-one

methylamine
74-89-5

methylamine

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
In methanol; water at 60℃; for 4h;71.2%
3-[(2-methoxycarbonyl-propyl)-methyl-amino]-butyric acid ethyl ester
897400-05-4

3-[(2-methoxycarbonyl-propyl)-methyl-amino]-butyric acid ethyl ester

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
Stage #1: 3-[(2-methoxycarbonyl-propyl)-methyl-amino]-butyric acid ethyl ester With ethanol; sodium In xylenes at 20 - 75℃; for 8h; Heating / reflux;
Stage #2: With hydrogenchloride In water for 6h; Heating / reflux;
Stage #3: With potassium hydroxide In water at 0℃; pH=10;
47%
N-(1,2,5-trimethylpiperidylidene-4)aniline
60585-74-2, 127611-57-8, 127611-58-9, 127611-59-0

N-(1,2,5-trimethylpiperidylidene-4)aniline

benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

A

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

B

1-methyl-2r,5c-dimethyl-4t-benzyl-4c-phenylaminopiperidine
129115-34-0

1-methyl-2r,5c-dimethyl-4t-benzyl-4c-phenylaminopiperidine

C

aniline
62-53-3

aniline

Conditions
ConditionsYield
In diethyl ether for 8h; Heating;A n/a
B 46%
C n/a
5-ethoxy-2-methyl-1-hexen-3-one
103263-54-3

5-ethoxy-2-methyl-1-hexen-3-one

methylamine
74-89-5

methylamine

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
In methanol; water at 60℃; for 4h;45.5%
phenyllithium
591-51-5

phenyllithium

N-(1,2,5-trimethylpiperidinylidene-4-)-β-hydroxyethylamine
113556-34-6

N-(1,2,5-trimethylpiperidinylidene-4-)-β-hydroxyethylamine

A

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

B

ethanolamine
141-43-5

ethanolamine

C

1,2,5-trimethyl-4-phenyl-4-N-(β-hydroxyethyl)aminopiperidine
113556-41-5

1,2,5-trimethyl-4-phenyl-4-N-(β-hydroxyethyl)aminopiperidine

Conditions
ConditionsYield
In diethyl etherA n/a
B n/a
C 11%
2,5-dimethyl-tetrahydro-pyran-4-one
66109-81-7

2,5-dimethyl-tetrahydro-pyran-4-one

methylamine
74-89-5

methylamine

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
With water
2,5-dimethylpiperidin-4-one
4558-87-6

2,5-dimethylpiperidin-4-one

methyl iodide
74-88-4

methyl iodide

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
With 1,4-dioxane
2-methyl-hexa-1,5-dien-3-yne
820-54-2

2-methyl-hexa-1,5-dien-3-yne

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
With water; butan-1-ol Erwaermen unter Zusatz von Schwefelsaeure und Quecksilber(II)-sulfat und Erwaermen des Reaktionsgemisches mit wss. Methylamin in Aethanol;
(E)-2-methylhexa-1,4-dien-3-one
13058-39-4, 105645-96-3, 105645-99-6

(E)-2-methylhexa-1,4-dien-3-one

methylamine
74-89-5

methylamine

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
With water
1,5-dimethoxy-2-methyl-hexan-3-one
41854-15-3

1,5-dimethoxy-2-methyl-hexan-3-one

methylamine
74-89-5

methylamine

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
With water
2,5-dimethyl-tetrahydro-pyran-4-one
66109-81-7

2,5-dimethyl-tetrahydro-pyran-4-one

water
7732-18-5

water

methylamine
74-89-5

methylamine

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

3-Methyl-3-buten-2-one
814-78-8

3-Methyl-3-buten-2-one

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 82.3 percent / NaI, Et3N / acetonitrile / 1 h / 70 °C
2: 60.6 percent / ZnCl2 / ethyl acetate / 1 h / 40 °C
3: 45.5 percent / methanol; H2O / 4 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: 82.3 percent / NaI, Et3N / acetonitrile / 1 h / 70 °C
2: 68.2 percent / ZnCl2 / ethyl acetate / 1 h / 40 °C
3: 71.2 percent / methanol; H2O / 4 h / 60 °C
View Scheme
2-methyl-3-<(trimethylsilyl)oxy>-1,3-butadiene
54781-31-6

2-methyl-3-<(trimethylsilyl)oxy>-1,3-butadiene

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60.6 percent / ZnCl2 / ethyl acetate / 1 h / 40 °C
2: 45.5 percent / methanol; H2O / 4 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: 68.2 percent / ZnCl2 / ethyl acetate / 1 h / 40 °C
2: 71.2 percent / methanol; H2O / 4 h / 60 °C
View Scheme
C13H25NO4
1252678-29-7

C13H25NO4

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

Conditions
ConditionsYield
Stage #1: C13H25NO4 With sodium In 5,5-dimethyl-1,3-cyclohexadiene; ethanol Dieckmann reaction; Reflux;
Stage #2: With hydrogenchloride In water Reflux;
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

3-methyl-2-pyrazoline-5-one
108-26-9

3-methyl-2-pyrazoline-5-one

malononitrile
109-77-3

malononitrile

C15H21N5O

C15H21N5O

Conditions
ConditionsYield
In ethanol at 20℃; for 12h;94%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

acetic acid hydrazide
1068-57-1

acetic acid hydrazide

1,2,5-Trimethyl-4-piperidone acetylhydrazone
102689-09-8

1,2,5-Trimethyl-4-piperidone acetylhydrazone

Conditions
ConditionsYield
at 20℃; for 0.25h;90%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

2-aminoethyl vinyl ether
7336-29-0

2-aminoethyl vinyl ether

1,2,5-trimethyl-4-(β-vinyloxyethylimino)piperidine
72310-54-4

1,2,5-trimethyl-4-(β-vinyloxyethylimino)piperidine

Conditions
ConditionsYield
In benzene Heating;85%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

(-)-1,2,5-trimethyl-4-(1S-phenylethylimino)piperidine

(-)-1,2,5-trimethyl-4-(1S-phenylethylimino)piperidine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;85%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

1,2,5-trimethylpiperidine-4-one oxime
113849-83-5, 131485-23-9

1,2,5-trimethylpiperidine-4-one oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol for 4h; Heating;81%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

acetonitrile
75-05-8

acetonitrile

N-(4-Acetylamino-1,2,5-trimethyl-piperidin-4-yl)-acetamide

N-(4-Acetylamino-1,2,5-trimethyl-piperidin-4-yl)-acetamide

Conditions
ConditionsYield
With sulfuric acid at 60℃; for 2h;81%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

benzylamine
100-46-9

benzylamine

N-(1-methyl-2,5-dimethyl-4-piperidylidene)benzylamine
113556-33-5

N-(1-methyl-2,5-dimethyl-4-piperidylidene)benzylamine

Conditions
ConditionsYield
With zinc(II) chloride In toluene Heating; catalytic amount of acetic acid, benzene;76.5%
In toluene Heating;
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

aniline
62-53-3

aniline

N-(1,2,5-trimethylpiperidylidene-4)aniline
60585-74-2, 127611-57-8, 127611-58-9, 127611-59-0

N-(1,2,5-trimethylpiperidylidene-4)aniline

Conditions
ConditionsYield
With acetic acid In toluene Heating;72%
With toluene-4-sulfonic acid In benzene Heating;71.3%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

N-(1,2,5-trimethylpiperidylidene-4-)-γ-hydroxypropylamine
113556-47-1

N-(1,2,5-trimethylpiperidylidene-4-)-γ-hydroxypropylamine

Conditions
ConditionsYield
With zinc(II) chloride In toluene Heating; catalytic amount of acetic acid, benzene;72%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

1,2,5-trimethyl-4-naphthalen-1-ylethynyl-piperidin-4-ol
40964-05-4

1,2,5-trimethyl-4-naphthalen-1-ylethynyl-piperidin-4-ol

Conditions
ConditionsYield
Stage #1: 1-ethynylnaphthalene With n-butyllithium In tetrahydrofuran; hexanes at 0 - 20℃; for 1.08333h;
Stage #2: 1,2,5-trimethyl-4-piperidone In tetrahydrofuran; hexanes at 20℃; for 1h;
67%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

diethyldiethynylsilane
18292-19-8

diethyldiethynylsilane

β-isomer of 4-<(diethylethynylsilyl)ethynyl>-1,2,5-trimethyl-4-piperidinol

β-isomer of 4-<(diethylethynylsilyl)ethynyl>-1,2,5-trimethyl-4-piperidinol

γ-isomer of 4-<(diethylethynylsilyl)ethynyl>-1,2,5-trimethyl-4-piperidinol

γ-isomer of 4-<(diethylethynylsilyl)ethynyl>-1,2,5-trimethyl-4-piperidinol

Conditions
ConditionsYield
With ethylmagnesium bromide In diethyl ether at 80 - 90℃; for 2h;A 17.55%
B 52.45%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

N-methyl-N-propargylaniline
4282-82-0

N-methyl-N-propargylaniline

1,2,5-trimethyl-4-hydroxy-4-<3-(N-methyl-N-phenylamino)-propynyl>piperidine

1,2,5-trimethyl-4-hydroxy-4-<3-(N-methyl-N-phenylamino)-propynyl>piperidine

1,2,5-trimethyl-4-hydroxy-4-<3-(N-methyl-N-phenylamino)-propynyl>piperidine

1,2,5-trimethyl-4-hydroxy-4-<3-(N-methyl-N-phenylamino)-propynyl>piperidine

1,2,5-trimethyl-4-hydroxy-4-<3-(N-methyl-N-phenylamino)-propynyl>piperidine

1,2,5-trimethyl-4-hydroxy-4-<3-(N-methyl-N-phenylamino)-propynyl>piperidine

Conditions
ConditionsYield
With potassium hydroxide In diethyl ether for 8h; Ambient temperature;A 8%
B 32%
C 51%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

aniline
62-53-3

aniline

1,2,5-trimethyl-4-N-phenyliminopiperidine
60585-74-2, 127611-57-8, 127611-58-9, 127611-59-0

1,2,5-trimethyl-4-N-phenyliminopiperidine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;50%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

C14H21N3
83821-86-7

C14H21N3

B

N-[1,2,5-Trimethyl-piperidin-(4Z)-ylidene]-benzene-1,2-diamine
83821-90-3

N-[1,2,5-Trimethyl-piperidin-(4Z)-ylidene]-benzene-1,2-diamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;A 5%
B 50%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

N-(1-methyl-2,5-dimethyl-4-piperidylidene)-α-phenylethylamine
142917-25-7

N-(1-methyl-2,5-dimethyl-4-piperidylidene)-α-phenylethylamine

Conditions
ConditionsYield
In toluene Heating;49%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

m,p-dichloroaniline
95-76-1

m,p-dichloroaniline

N-(1,2,5-trimethyl-4-piperidylidene)-3,4-dichloroaniline
136038-82-9

N-(1,2,5-trimethyl-4-piperidylidene)-3,4-dichloroaniline

Conditions
ConditionsYield
With acetic acid In toluene for 8h; Heating;40%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

4-p-dimethylaminophenyl-3-buten-2-one
5432-53-1

4-p-dimethylaminophenyl-3-buten-2-one

4a-hydroxy-8-(p-dimethylaminophenyl)-2,3,8a-trimethyldecahydro-6-isoquinolone

4a-hydroxy-8-(p-dimethylaminophenyl)-2,3,8a-trimethyldecahydro-6-isoquinolone

Conditions
ConditionsYield
Stage #1: 1,2,5-trimethyl-4-piperidone With sodium hydride In water; N,N-dimethyl-formamide at 20℃; Mannich reaction;
Stage #2: 4-p-dimethylaminophenyl-3-buten-2-one In water; N,N-dimethyl-formamide at 20℃; Mannich reaction;
40%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

ethanolamine
141-43-5

ethanolamine

N-(1,2,5-trimethylpiperidinylidene-4-)-β-hydroxyethylamine
113556-34-6

N-(1,2,5-trimethylpiperidinylidene-4-)-β-hydroxyethylamine

Conditions
ConditionsYield
With zinc(II) chloride In toluene Heating; catalytic amount of acetic acid, benzene;35%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

1-Phenylbut-1-en-3-one
122-57-6

1-Phenylbut-1-en-3-one

4a-hydroxy-2,3,8a-trimethyl-8-phenyldecahydro-6-isoquinolone

4a-hydroxy-2,3,8a-trimethyl-8-phenyldecahydro-6-isoquinolone

Conditions
ConditionsYield
Stage #1: 1,2,5-trimethyl-4-piperidone With sodium hydride In water; N,N-dimethyl-formamide at 20℃; for 1h; Mannich reaction;
Stage #2: 1-Phenylbut-1-en-3-one In water; N,N-dimethyl-formamide at 20℃; for 72h; Mannich reaction;
34%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

2,2,6,6-Tetramethyl-4-piperidone
826-36-8

2,2,6,6-Tetramethyl-4-piperidone

C20H30N2S

C20H30N2S

Conditions
ConditionsYield
With sulfuric acid at 60 - 65℃; for 4h;32%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

ortho-cresol
95-48-7

ortho-cresol

trans-1,2,5-Trimethyl-4-(4-hydroxy-3-methylphenyl)-Δ3-tetrahydropyridine
108332-84-9

trans-1,2,5-Trimethyl-4-(4-hydroxy-3-methylphenyl)-Δ3-tetrahydropyridine

Conditions
ConditionsYield
With boron trifluoride diethyl etherate31%
2-thiazolylamine
96-50-4

2-thiazolylamine

1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

1,2,5-trimethyl-4-(2-thiazolyl)iminopiperidine
139117-78-5

1,2,5-trimethyl-4-(2-thiazolyl)iminopiperidine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;30%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

1,3-diphenyl-propen-3-one
614-47-1

1,3-diphenyl-propen-3-one

1,2,5-trimethyl-3-(3-oxo-1,3-diphenylpropyl)piperidin-4-one

1,2,5-trimethyl-3-(3-oxo-1,3-diphenylpropyl)piperidin-4-one

B

6-hydroxy-1,3,4-trimethyl-6,8-diphenyl-3-azabicyclo[3.3.1]nonan-9-one hydrochloride

6-hydroxy-1,3,4-trimethyl-6,8-diphenyl-3-azabicyclo[3.3.1]nonan-9-one hydrochloride

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 5h; Michael reaction;A 6.39%
B 23.2%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

4-(2-methoxy-naphthalen-1-ylethynyl)-1,2,5-trimethyl-piperidin-4-ol

4-(2-methoxy-naphthalen-1-ylethynyl)-1,2,5-trimethyl-piperidin-4-ol

Conditions
ConditionsYield
Stage #1: 1-(2',2'-dibromovinyl)-2-methoxynaphthalene With n-butyllithium In tetrahydrofuran; hexanes at -78 - 20℃; for 1.5h;
Stage #2: 1,2,5-trimethyl-4-piperidone In tetrahydrofuran; hexanes at 20℃; for 0.25h;
19%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

carbon disulfide
75-15-0

carbon disulfide

sodium cyanide
143-33-9

sodium cyanide

1,2,5-trimethylpiperidine-4-spiro-5'-imidazolidine-2',4'-dithione

1,2,5-trimethylpiperidine-4-spiro-5'-imidazolidine-2',4'-dithione

Conditions
ConditionsYield
With ammonium chloride In ethanol at 50 - 55℃; for 24h;18%
1,2,5-trimethyl-4-piperidone
7516-33-8

1,2,5-trimethyl-4-piperidone

(2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one
22966-09-2

(2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one

8-(4-bromophenyl)-6-hydroxy-1,3,4-trimethyl-6-phenyl-3-azabicyclo[3.3.1]nonan-9-one hydrochloride

8-(4-bromophenyl)-6-hydroxy-1,3,4-trimethyl-6-phenyl-3-azabicyclo[3.3.1]nonan-9-one hydrochloride

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water; benzene for 48h; Michael reaction;14.6%

7516-33-8Relevant articles and documents

NEW PATH OF SYNTHESIS OF 1,2,5-TRIMETHYL-4-PIPERIDONE

Makin, S. M.,Nazarova, O. N.,Kundryutskova, L. A.

, p. 1022 - 1024 (1989)

-

4-PIPERIDINOL TERTIARY AMINES AS HISTAMINE 3 RECEPTOR INHIBITORS FOR THE TREATMENT OF OBESITY AND OTHER CNS DISORDERS

-

Page/Page column 15-16, (2008/06/13)

This invention relates to compounds having pharmacological activity, to compositions containing these compounds, and to a method of treatment employing the compounds and compositions. More particularly, this invention concerns certain non-imidazole tertiary amine derivatives and their salts and solvates. These compounds have H3 histamine receptor antagonist activity. This invention also relates to pharmaceutical compositions containing these compounds and to a method of treating disorders in which histamine H3 receptor blockade is beneficial.

ASYMMETRIC SYNTHESIS AND ABSOLUTE CONFIGURATION OF 1-α-PHENYLETHYL-2,5-DIMETHYL-4-PIPERIDONE ISOMERS

Grishina, G. V.,Potapov, V. M.,Abdulganeeva, S. A.,Gudasheva, T. A.,Karapetyan, A. A.,et al.

, p. 1327 - 1333 (2007/10/02)

Reaction of the methyl iodide of trans-1,2-5-trimethyl-4-piperidone with S-α-phenylethylamine proceeds asymmetrically and leads in 66percent optical yield to the formation of the cis- and trans-diastereomeric pair of 1-(α-phenylethyl)-2,5-dimethyl-4-piperidone, in which the new asymmetric centers possess the 2S,5S- and 2S,5R-configurations, respectively.According to x-ray structural analysis, the minor trans-1-(α-phenylethyl)-2,5-dimethyl-4-piperidone component possesses the 2R,5S-configuration.The occurrence of asymmetric synthesis accompanying transamination was confirmed via the preparation of enantiomers of trans-2,5- and trans-1,2,5-trimethyl-4-piperidones.

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