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Cas Database

73873-63-9

73873-63-9

Identification

  • Product Name:1-methyl-trans-4-methoxycyclohexanecarboxylic acid

  • CAS Number: 73873-63-9

  • EINECS:

  • Molecular Weight:172.224

  • Molecular Formula: C9H16O3

  • HS Code:

  • Mol File:73873-63-9.mol

Synonyms:1-methyl-trans-4-methoxycyclohexanecarboxylic acid

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Relevant articles and documentsAll total 4 Articles be found

The discovery of a series of N-substituted 3-(4-piperidinyl)-1,3- benzoxazolinones and oxindoles as highly brain penetrant, selective muscarinic M1 agonists

Johnson, Dale J.,Forbes, Ian T.,Watson, Steve P.,Garzya, Vincenzo,Stevenson, Graeme I.,Walker, Graham R.,Mudhar, Harminder S.,Flynn, Sean T.,Wyman, Paul A.,Smith, Paul W.,Murkitt, Graham S.,Lucas, Adam J.,Mookherjee, Claudette R.,Watson, Jeannette M.,Gartlon, Jane E.,Bradford, Andrea M.,Brown, Fiona

scheme or table, p. 5434 - 5438 (2011/02/21)

A series of N-substituted 3-(4-piperidinyl)-1,3-benzoxazolinones and oxindoles are reported which were found to be potent and selective muscarinic M1 agonists. By control of the physicochemical characteristics of the series, particularly the li

COMPOUNDS WHICH HAVE ACTIVITY AT M1 RECEPTOR AND THEIR USES IN MEDICINE

-

Page/Page column 88-89, (2009/04/25)

Compounds of formula (I) or a salt thereof are provided: wherein R4, R5, R6, Q, A, Y and R are as defined in the description. Uses of the compounds as medicaments and in the manufacture of medicaments for treating psychotic disorders, cognitive impairments and Alzheimer's Disease are disclosed. The invention further discloses pharmaceutical compositions comprising the compounds.

BENZIMIDAZOLES WHICH HAVE ACTIVITY AT M1 RECEPTOR AND THEIR USES IN MEDICINE

-

, (2008/06/13)

Compounds of formula (I), salts and solvates are provided: formula (I), wherein Q, R and R6 are as defined in the claims. Uses of the compounds for therapy, for example in the treatment of psychotic disorders and cognitive impairment, are also disclosed.

Stereochemistry of Alkylation of Carboxylic Acid Salt and Ester α Anions Derived from Cyclic Systems.

Krapcho, A.Paul,Dundulis, Edward A.

, p. 3236 - 3245 (2007/10/02)

A stereochemical study of the alkylation of α-lithiated carboxylate salts and esters has been performed.The α anions derived from the bicyclic acids exo-1, endo-1, and 7 (R=H) and the esters 4 and 7 (R=CH3) yield predominantly exo alkylation.As an example, the α anion derived from ester 7 (R=CH3) on treatment with CH3I yields exo-8 (R=R'=CH3) and endo-9 (R=R'=CH3) in a 97:3 ratio, a highly stereoselective reaction.Addition of TMEDA to the reactions involving the α anions derived from exo- or endo-1 did not change the stereochemical alkylation results.The α anions derived from the substituted cyclohexanecarboxylic acids 10, 13, 16, 19, or 22 (where R=H in each case) on methylation yield more axial methylation (axial/equatorial ratios of 0.4-2.7) than the α anions derived from the methyl esters corresponding to these acids.The α anions from the esters yield predominantly equatorial methylated products (e/a ratios varying from 4 to 9).The reasons for the different stereochemical results are discussed.

Process route upstream and downstream products

Process route

cis/trans-1-methyl-4-(methyloxy)cyclohexanecarboxylic acid chloride

cis/trans-1-methyl-4-(methyloxy)cyclohexanecarboxylic acid chloride

1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

Conditions
Conditions Yield
cis/trans-1-methyl-4-(methyloxy)cyclohexanecarboxylic acid chloride; With sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 0.5h;
With hydrogenchloride; In water;
With sodium carbonate; In tetrahydrofuran; hexane; at 20 ℃; for 0.5h;
methyl iodide
74-88-4

methyl iodide

cis-1-methyl-4-(methyloxy)cyclohexanecarboxylic acid

cis-1-methyl-4-(methyloxy)cyclohexanecarboxylic acid

1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

Conditions
Conditions Yield
4-methoxycyclohexylcarboxylic acid; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at 0 - 50 ℃; for 2.16667h;
methyl iodide; In tetrahydrofuran; hexane; at 20 ℃; for 2h;
cis/trans-1-methyl-4-(methyloxy)cyclohexanecarboxylic acid
150864-93-0

cis/trans-1-methyl-4-(methyloxy)cyclohexanecarboxylic acid

1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

Conditions
Conditions Yield
With thionyl chloride; In toluene; at 85 ℃;
Multi-step reaction with 2 steps
1: thionyl chloride / 4 h / 90 °C / Heating / reflux
2: sodium carbonate / tetrahydrofuran; hexane / 0.5 h / 20 °C
With thionyl chloride; sodium carbonate; In tetrahydrofuran; hexane;
4-methoxycyclohexylcarboxylic acid
95233-12-8

4-methoxycyclohexylcarboxylic acid

methyl iodide
74-88-4

methyl iodide

1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

1-Methyl-cis-4-methoxycyclohexanecarboxylic acid
73873-65-1

1-Methyl-cis-4-methoxycyclohexanecarboxylic acid

Conditions
Conditions Yield
With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -75 ℃; Product distribution; various temperatures;
With n-butyllithium; diisopropylamine; Yield given. Multistep reaction. Yields of byproduct given; 1) anhydrous THF a) 0.5h, -75 deg C b) room temperature c) 2h, 50 deg C 2) 1,5h, room temperature;
With n-butyllithium; diisopropylamine; Yield given. Multistep reaction. Yields of byproduct given; 1) anhydrous THF a) 0.5h -75 deg C b) room temperature c) 2h 50 deg C 2) 1.5h room temperature;
1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

trans-1-isocyanato-1-methyl-4-(methyloxy)cyclohexane
950773-02-1

trans-1-isocyanato-1-methyl-4-(methyloxy)cyclohexane

Conditions
Conditions Yield
With diphenyl phosphoryl azide; triethylamine; In toluene; at 20 - 80 ℃; for 2h;
48%
With diphenyl phosphoryl azide; triethylamine; In toluene; at 20 - 80 ℃; for 2h; Heating / reflux;
48%
With diphenyl phosphoryl azide; triethylamine; In toluene; at 90 ℃;
1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

N-(5-fluoro-2-nitrophenyl)-1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinamine
950773-06-5

N-(5-fluoro-2-nitrophenyl)-1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinamine

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 20 - 80 °C / Heating / reflux
2: hydrogenchloride / tetrahydrofuran; water / 4 h / 20 °C
3: potassium carbonate / ethanol; water / 80 °C / Heating / reflux
4: ammonia; hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 2585.81 Torr
5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 100 °C / Microwave reactor
With hydrogenchloride; diphenyl phosphoryl azide; ammonia; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;
1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

6-fluoro-1-{1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one

6-fluoro-1-{1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 20 - 80 °C / Heating / reflux
2: hydrogenchloride / tetrahydrofuran; water / 4 h / 20 °C
3: potassium carbonate / ethanol; water / 80 °C / Heating / reflux
4: ammonia; hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 2585.81 Torr
5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 100 °C / Microwave reactor
6: hydrazine / nickel / ethanol; water / 1 h
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C
With hydrogenchloride; diphenyl phosphoryl azide; ammonia; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; hydrazine; palladium 10% on activated carbon; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

6-fluoro-1-{1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

6-fluoro-1-{1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 20 - 80 °C / Heating / reflux
2: hydrogenchloride / tetrahydrofuran; water / 4 h / 20 °C
3: potassium carbonate / ethanol; water / 80 °C / Heating / reflux
4: ammonia; hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 2585.81 Torr
5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 100 °C / Microwave reactor
6: hydrazine / nickel / ethanol; water / 1 h
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C
8: hydrogenchloride / methanol; diethyl ether / 0.5 h
With hydrogenchloride; diphenyl phosphoryl azide; ammonia; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; hydrazine; palladium 10% on activated carbon; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinamine
950773-05-4

1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinamine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 20 - 80 °C / Heating / reflux
2: hydrogenchloride / tetrahydrofuran; water / 4 h / 20 °C
3: potassium carbonate / ethanol; water / 80 °C / Heating / reflux
4: ammonia; hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 2585.81 Torr
With hydrogenchloride; diphenyl phosphoryl azide; ammonia; hydrogen; potassium carbonate; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran; methanol; ethanol; water; toluene;
1-methyl-trans-4-methoxycyclohexanecarboxylic acid
73873-63-9

1-methyl-trans-4-methoxycyclohexanecarboxylic acid

(2-amino-5-fluorophenyl){1-[trans-4-(methyloxy)-1-methylcyclohexyl]-4-piperidinyl}amine
950773-07-6

(2-amino-5-fluorophenyl){1-[trans-4-(methyloxy)-1-methylcyclohexyl]-4-piperidinyl}amine

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 20 - 80 °C / Heating / reflux
2: hydrogenchloride / tetrahydrofuran; water / 4 h / 20 °C
3: potassium carbonate / ethanol; water / 80 °C / Heating / reflux
4: ammonia; hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C / 2585.81 Torr
5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 100 °C / Microwave reactor
6: hydrazine / nickel / ethanol; water / 1 h
With hydrogenchloride; diphenyl phosphoryl azide; ammonia; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; hydrazine; palladium 10% on activated carbon; nickel; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

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