2981-10-4

Basic information

• Product Name: 1-(1-PIPERIDINO)CYCLOHEXENE
• Synonyms: 1-Piperidinylcyclohexene;N-(1-Cyclohexen-1-yl)piperidine;N-(1-Cyclohexenyl)piperidine;1-(1-CYCLOHEXENYL)PIPERIDINE;1-(1-PIPERIDINO)CYCLOHEXENE;1-CYCLOHEX-1-ENYL-PIPERIDINE;1-(CYCLOHEXEN-1-YL)PIPERIDINE;CYCLOHEXENYLPIPERIDINE
• CAS NO: 2981-10-4
• Molecular Formula: C₁₁H₁₉N
• Molecular Weight: 165.28
• Product Categories: API intermediates
• Mol File: 2981-10-4.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 120-122°C 16mm
• Flash Point: 120-122°C/16mm
• Appearance: Clear yellow/Liquid
• Density: 0.978g/cm³
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: 1.5140
• Storage Temp.: Refrigerator (+4°C)
• PKA: 8.88±0.20(Predicted)
• BRN: 113990
• CAS DataBase Reference: 1-(1-PIPERIDINO)CYCLOHEXENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-PIPERIDINO)CYCLOHEXENE(2981-10-4)
• EPA Substance Registry System: 1-(1-PIPERIDINO)CYCLOHEXENE(2981-10-4)

Safety Data

• Statements: 22-36/38
• Safety Statements: 26-36/37/39
• RTECS: TM6510000
• Hazardous Substances Data: 2981-10-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow liquid

InChI:InChI=1/C11H19N/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h7H,1-6,8-10H2

Synthetic route

piperidine (110-89-4) + cyclohexanone (108-94-1) → 1-(cyclohex-1-en-1-yl)piperidine (2981-10-4)

Conditions	Yield
With Montmorillonite K 10 clay for 0.133333h; microwave (160 Watts) irradiation;	95%
Envirocat EPZG for 0.0333333h; Irradiation;	90%
With K-10 Montmorillonite clay In toluene for 3h; Heating;	86%

lithium piperidide (4442-11-9) + cyclohexanone (108-94-1) → 1-(cyclohex-1-en-1-yl)piperidine (2981-10-4)

Conditions	Yield
With tin(ll) chloride 1) Et2O, r.t., 2 h, 2) r.t.; Yield given. Multistep reaction;

piperidine (110-89-4) + cyclohexanone (108-94-1) + CaO → 1-(cyclohex-1-en-1-yl)piperidine (2981-10-4)

Conditions	Yield
anschl. Destillieren unter 100 Torr;

piperidine (110-89-4) + cyclohexene (110-83-8) → 1-(cyclohex-1-en-1-yl)piperidine (2981-10-4)

Conditions	Yield
With toluene-4-sulfonic acid In benzene

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) → 1-cyclohexylpiperidine (3319-01-5)

Conditions	Yield
With 2-[bis(pentafluorophenyl)boryl]-N,N-dimethylaniline In benzene-d6 at 80℃; under 1500.15 Torr; for 1h; Inert atmosphere;	100%
With butyl triphenylphosphonium tetraborate at 20℃; for 0.0833333h;	96%
With sodium tetrahydroborate; hydrogen; nickel dichloride In isopropyl alcohol at 60℃; under 760.051 Torr; for 6h;	92%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 2-benzylidene-1-tetralone (6261-32-1) → 5,6,7a,8,9,10,11,11a-Octahydro-7-phenyl-11a-piperidinobenzo-7H-xanthene (32631-50-8)

Conditions	Yield
With molecular sieve In toluene for 20h; Heating;	99%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 3-Benzyliden-2,3-dihydro-4H-1-benzothiopyran-4-on-1,1-dioxid (101001-24-5) → 7,7a,8,9,10,11-Hexahydro-7-phenyl-11a-piperidino-6H,11aH-<1>benzothiopyrano<4,3-b>chromen-5,5-dioxid (93362-80-2)

Conditions	Yield
In methanol for 0.5h; Ambient temperature;	98%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 3-diazonium-o-carborane tetrafluoroborate → 2-carboranylcyclohexanone

Conditions	Yield
With lithium diisopropyl amide In hexane at -30 - 20℃; for 0.166667h; Ene Reaction; Inert atmosphere; regioselective reaction;	98%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + C5H5RuP(C6H5)2CH2P(C6H5)2(CH2SO2)(1+)*PF6(1-)={(C5H5)Ru(P(C6H5)2CH2P(C6H5)2)(CH2SO2)}PF6 → {C5H5Ru((C6H5)2PCH2P(C6H5)2)(SO2CH2C6H9NC5H10)}(1+)*PF6(1-)={C5H5Ru((C6H5)2PCH2P(C6H5)2)(SO2CH2C6H9NC5H10)}PF6

Conditions	Yield
In dichloromethane addn. of C6H9NC5H10 to soln. of Ru sulfene complex in CH2Cl2 at 20°C under N2 and stirring for 1 h;; concn.; addn. of petroleum ether; pptn.; elem. anal.;;	97%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-(4-methoxybenzylidene)-p-toluenesulfonamide (14674-38-5) → N-((2-oxocyclohexyl)(4-methoxyphenyl)methyl)-p-toluenesulfonamide + N-((2-oxocyclohexyl)(4-methoxyphenyl)methyl)-p-toluenesulfonamide

Conditions	Yield
With acetic acid In dichloromethane; water at -45℃; for 3h; Inert atmosphere; diastereoselective reaction;	A 97% B n/a

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-(2-naphthylidene)-4-methylbenzenesulfonamide (17692-84-1) → N-((2-(piperidin-1-yl)cyclohexyl)(2-naphthyl)methyl)-p-toluenesulfonamide

Conditions	Yield
Stage #1: 1-(cyclohex-1-en-1-yl)piperidine; N-(2-naphthylidene)-4-methylbenzenesulfonamide With acetic acid In dichloromethane; water at -78℃; for 3h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol; dichloromethane; water at -45℃; for 1h; Inert atmosphere; diastereoselective reaction;	97%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-methanesulfonyl benzylideneamine (73845-05-3, 108440-09-1, 14674-34-1) → N-((2-oxocyclohexyl)(phenyl)methyl)methanesulfonamide

Conditions	Yield
With acetic acid In dichloromethane; water at -78℃; for 6h; Inert atmosphere; diastereoselective reaction;	96%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-(2-naphthylidene)-4-methylbenzenesulfonamide (17692-84-1) → N-[2-(piperidin-1-yl)cyclohexyl](2-naphthyl)methyl-p-toluenesulfonamide

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; trichlorosilane In dichloromethane at -40℃; for 1h; Inert atmosphere; diastereoselective reaction;	95%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-(2-naphthylidene)-4-methylbenzenesulfonamide (17692-84-1) → N-((2-oxocyclohexyl)(2-naphthyl)methyl)-p-toluenesulfonamide

Conditions	Yield
With acetic acid In dichloromethane; water at -78℃; for 3h; Inert atmosphere; diastereoselective reaction;	95%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + methyl 3-phenyl-3-chloro-2-ketopropionate (32803-73-9) → 2-phenyl-1-(1-piperidinyl)ethanone (3626-62-8) + methyl 1-(5-chloropentyl)-2-phenyl-4,5,6,7-tetrahydro-1H-indole-3-carboxylate + piperidine hydrochloride (6091-44-7)

Conditions	Yield
In 1,4-dioxane for 2h; Reflux;	A 4% B 95% C 1%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) → N-((2-(piperidin-1-yl)cyclohexyl)(phenyl)methyl)-p-toluenenesulfonamide

Conditions	Yield
Stage #1: 1-(cyclohex-1-en-1-yl)piperidine; N-(benzylidene)-p-methylbenzenesulfonamide With acetic acid In dichloromethane; water at -78℃; for 3h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol; dichloromethane; water at -45℃; for 1h; Inert atmosphere; diastereoselective reaction;	93%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-methanesulfonyl benzylideneamine (73845-05-3, 108440-09-1, 14674-34-1) → N-((2-(piperidin-1-yl)cyclohexyl)(phenyl)methyl)methanenesulfonamide

Conditions	Yield
Stage #1: 1-(cyclohex-1-en-1-yl)piperidine; N-methanesulfonyl benzylideneamine With acetic acid In dichloromethane; water at -78℃; for 6h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol; dichloromethane; water at -45℃; for 1h; Inert atmosphere; diastereoselective reaction;	92%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 1-(γ-phenylallyl)benzotriazole (171193-30-9) → 2-[(E)-3-phenyl-2-propenyl]cyclohexanone (84624-35-1) + 2-[(Z)-3-phenyl-2-propenyl]cyclohexanone

Conditions	Yield
Stage #1: 1-(γ-phenylallyl)benzotriazole With palladium diacetate; triphenylphosphine; zinc dibromide In benzene for 0.25h; Elimination; Heating; Stage #2: 1-(cyclohex-1-en-1-yl)piperidine In benzene Addition; Heating; Stage #3: With water for 0.5h; Hydrolysis; Heating;	A 91% B n/a

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 2-furaldehyde tosylimine (13707-47-6) → N-((2-oxocyclohexyl)(2-furyl)methyl)-p-toluenesulfonamide + N-((2-oxocyclohexyl)(2-furyl)methyl)-p-toluenesulfonamide

Conditions	Yield
With acetic acid In dichloromethane; water at -78℃; for 3h; Inert atmosphere; diastereoselective reaction;	A n/a B 91%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + quinazoline-4-carbonitrile (36082-71-0) → 4-(piperidin-1-yl)-quinazoline (41229-10-1)

Conditions	Yield
In xylene for 24h; Heating;	90%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 1,3-diphenyl-propen-3-one (614-47-1) → 4a,5,6,7,8,8a-Hexahydro-2,4-diphenyl-8a-piperidino-4H-chromene (78019-12-2)

Conditions	Yield
In dichloromethane; Petroleum ether for 72h;	90%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 1-[1-(3-methyl-butyl)-allyl]-1H-benzotriazole → 2-[(E)-6-methyl-2-heptenyl]cyclohexanone

Conditions	Yield
Stage #1: 1-[1-(3-methyl-butyl)-allyl]-1H-benzotriazole With palladium diacetate; triphenylphosphine; zinc dibromide In benzene for 0.25h; Elimination; complexation; Heating; Stage #2: 1-(cyclohex-1-en-1-yl)piperidine In benzene Addition; Heating; Stage #3: With water for 0.5h; Hydrolysis; Heating;	90%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-tosyl-4-nitrobenzaldimine (13707-46-5) → N-((2-oxocyclohexyl)(4-nitrophenyl)methyl)-p-toluenesulfonamide

Conditions	Yield
With acetic acid In dichloromethane; water at -78℃; for 24h; Inert atmosphere; diastereoselective reaction;	90%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-tosyl-4-nitrobenzaldimine (13707-46-5) → N-((2-(piperidin-1-yl)cyclohexyl)(4-nitrophenyl)methyl)-p-toluenesulfonamide

Conditions	Yield
Stage #1: 1-(cyclohex-1-en-1-yl)piperidine; N-tosyl-4-nitrobenzaldimine With acetic acid In dichloromethane; water at -78℃; for 24h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol; dichloromethane; water at -45℃; for 1h; Inert atmosphere; diastereoselective reaction;	90%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 3,6-Dihydro-5-methyl-6-oxo-1,3-diphenyl-1-pyrimidinium-4-olat (96807-23-7) → 1-Methyl-9,12-diphenyl-2-piperidino-9,12-diazatricyclo<6.2.2.02,7>dodecan-10,11-dion (104975-89-5)

Conditions	Yield
With hydroquinone In toluene for 1.5h; Heating;	89%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + dibenzylideneacetone (35225-79-7) → 1-[(4R,4aS,8aS)-4-Phenyl-2-((E)-styryl)-4,4a,5,6,7,8-hexahydro-chromen-8a-yl]-piperidine

Conditions	Yield
With zinc(II) chloride In benzene at 20℃; for 1h;	89%

1-morpholino-1-butene (56176-55-7) + 1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + O-tosyl-C-cyano-C-(ethoxycarbonyl)-formaldehyde-oxime + O-tosyl-C-dicyano-formaldehyde-oxime → (2-piperidin-1-yl-cyclohex-1-enylimino)-malononitrile (49845-16-1)

Conditions	Yield
	89%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) → N-((2-oxocyclohexyl)(phenyl)methyl)-p-toluenesulfonamide

Conditions	Yield
With acetic acid In dichloromethane; water at -78℃; for 3h; Inert atmosphere; diastereoselective reaction;	89%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + Z-3-benzylidene-1-thiochromanone (74074-09-2) → 7,7a,8,9,10,11-Hexahydro-7-phenyl-11a-piperidino-6H,11aH<1>benzothiopyrano<4,3-b>chromen (93362-79-9)

Conditions	Yield
In methanol for 16h; Ambient temperature;	87%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 1-[4-Methyl-1-(3-methyl-butyl)-1-vinyl-pentyl]-1H-benzotriazole → 2-(3-isopentyl-6-methyl-2-heptenyl)cyclohexanone

Conditions	Yield
Stage #1: 1-[4-Methyl-1-(3-methyl-butyl)-1-vinyl-pentyl]-1H-benzotriazole With palladium diacetate; triphenylphosphine; zinc dibromide In benzene for 0.25h; Elimination; complexation; Heating; Stage #2: 1-(cyclohex-1-en-1-yl)piperidine In benzene Addition; Heating; Stage #3: With water for 0.5h; Hydrolysis; Heating;	87%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + 2-trifluoroacetylamino-1,4-naphthoquinone → 2,3,4,5-tetrahydro-1H-benzocarbazole-6,11-dione (136480-17-6)

Conditions	Yield
Stage #1: 1-(cyclohex-1-en-1-yl)piperidine; 2-trifluoroacetylamino-1,4-naphthoquinone In toluene at 20℃; for 5h; Stage #2: With sodium hydroxide; air In water; toluene at 20℃; for 0.25h;	87%

1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) + N-(4-methoxybenzylidene)-p-toluenesulfonamide (14674-38-5) → N-((2-(piperidin-1-yl)cyclohexyl)(4-methoxyphenyl)methyl)-p-toluenesulfonamide

Conditions	Yield
Stage #1: 1-(cyclohex-1-en-1-yl)piperidine; N-(4-methoxybenzylidene)-p-toluenesulfonamide With acetic acid In dichloromethane; water at -45℃; for 3h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol; dichloromethane; water at -45℃; for 1h; Inert atmosphere; diastereoselective reaction;	87%

Succinimide (123-56-8) + 1-(cyclohex-1-en-1-yl)piperidine (2981-10-4) → 1-((1R,5S,6R)-6-Piperidin-1-yl-bicyclo[3.1.0]hex-6-yl)-pyrrolidine-2,5-dione

Conditions	Yield
With iodine; sodium methylate In methanol at 20℃; for 1h; Substitution; Cyclopropanation;	86%

Upstream product

• 110-89-4 piperidine 
• 108-94-1 cyclohexanone 
• 110-83-8 cyclohexene 
• 4442-11-9 lithium piperidide 

Downstream Products

• 10412-36-9 2-dichloromethylene-cyclohexanone 
• 5199-02-0 5-(2-piperidin-1-yl-cyclohex-1-enylmethylene)-2-thioxo-thiazolidin-4-one 
• 95948-87-1 2-phenyl-4-(2-piperidin-1-yl-cyclohex-1-enylmethylene)-4H-oxazol-5-one 
• 71964-86-8 11a-phenyl-4a-piperidin-1-yl-2,3,4,4a,11a,11b-hexahydro-1H-benzo[4,5]isoxazolo[2,3-a]indol-11-one 
• 62506-65-4 2-<(Dimethylhydrazono)ethyliden>cyclohexanon 
• 71964-78-8 1-oxy-2,3a-diphenyl-7a-piperidin-1-yl-3b,4,5,6,7,7a-hexahydro-3aH-benzo[d]pyrazolo[1,5-b]isoxazol-3-one 
• 71964-87-9 2,3,9b-triphenyl-5a-piperidin-1-yl-6,7,8,9,9a,9b-hexahydro-5aH-benzo[d]pyrrolo[1,2-b]isoxazol-1-one 
• 30018-90-7 2-dicyclohexylamino-5,6,7,8-tetrahydro-benzo[e][1,3]thiazine-4-thione 
• 57901-98-1 1-benzoyl-3-phenyl-4a-piperidin-1-yl-4a,5,6,7,8,8a-hexahydro-1H-benzo[1,3,4]oxadiazine 
• 19823-75-7 2-(2-propynyl)cyclohexanone 
• 90005-77-9 4,5,6,7-tetrahydrobenzo[d]isoxazole-3-carboxylic acid 
• 93947-43-4 3-phenyl-7a-piperidin-1-yl-3a,4,5,6,7,7a-hexahydro-benzo[d]isoxazole 
• 39076-63-6 2-phenyl-4a-piperidin-1-yl-4a,5,6,7,8,8a-hexahydro-benzo[e][1,3]oxazin-4-one 
• 39076-66-9 Cyclohexanon-⁽²⁾-carbonsaeure-benzoylamid 

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