142009-99-2|4-(Benzylamino)cyclohexan-1-one| Ambeed

CAS No. :	142009-99-2
Formula :	C₁₃H₁₇NO
M.W :	203.28
SMILES Code :	O=C1CCC(NCC2=CC=CC=C2)CC1
MDL No. :	MFCD06658335
InChI Key :	NMCDGVLRNAILQW-UHFFFAOYSA-N
Pubchem ID :	15932625

Safety of [ 142009-99-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335-H411
Precautionary Statements:	P273-P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 142009-99-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 142009-99-2 ]

[ 142009-99-2 ] Synthesis Path-Downstream 1~55

1
[ 131511-13-2 ]
[ 142009-99-2 ]

Yield	Reaction Conditions	Operation in experiment
95.6%	With hydrogenchloride; In water; at 20℃; for 22h;	Loaded with N-benzyl-1,4-dioxaspiro[4.5]silane-8-amine (16g, 64.69mmol, 1eq.)Of single-mouth bottle with 2mol/L HCl(81ml, 161.72mmol, 2.5eq.), stirred at room temperature overnight (12h),TLC (DCM:MeOH=25:1, 2 times) about half of the raw materials remained.After adding 2mol/L HCl (16ml, 0.5 eq.) for 10hTLC showed that the reaction was basically complete. Under the ice bath, Add NaOH (8g, about 3eq.) in water (about 24ml) solution,Adjust pH 910 with 2mol/L NaOH solution.Extract with dichloromethane (150+75+30 ml). The organic phase is combined,Wash with saturated sodium chloride (30ml), dry with anhydrous magnesium sulfate, filter with suction,The filtrate was evaporated under reduced pressure to obtain 12.57g of light brown liquid.The yield was 95.6%.

References: [1]Patent: CN112759538,2021,A .Location in patent: Paragraph 0176-0179.
[2]Tetrahedron,1997,vol. 53,p. 1391 - 1402.
[3]Tetrahedron Letters,1995,vol. 36,p. 1709 - 1712.
[4]Journal of Organic Chemistry,1995,vol. 60,p. 8089 - 8092.
[5]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.
[6]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.
[7]Organic Letters,2015,vol. 17,p. 568 - 571.
[8]Chemical Communications,2019,vol. 55,p. 8816 - 8819.

2
[ 142009-99-2 ]
[ 162338-03-6 ]

References: [1]Tetrahedron Letters,1995,vol. 36,p. 1709 - 1712.

3
[ 867-13-0 ]
[ 142009-99-2 ]
[ 172947-72-7 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 8089 - 8092.

4
[ 7677-24-9 ]
[ 142009-99-2 ]
4-Benzylamino-1-trimethylsilanyloxy-cyclohexanecarbonitrile [ No CAS ]
4-Benzylamino-1-trimethylsilanyloxy-cyclohexanecarbonitrile [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 1391 - 1402.

5
[ 24424-99-5 ]
[ 142009-99-2 ]
[ 188562-91-6 ]

Yield	Reaction Conditions	Operation in experiment
62.5%	With dmap; triethylamine; In dichloromethane; for 13h;	500ml three-necked bottle with thermometer and constant pressure dropping funnel4-(benzylamino)cyclohexane-1-one(35.7g, 175.61mmol, 1eq.), DCM (300ml),TEA (21.32g, 210.73mmol, 1.2eq.), DMAP (215mg, 1.76mmol, 0.01eq.),Stir in ice water bath. (Boc)2O (40.24 g,184.39mmol, 1.05eq.) in DCM (50ml).After adding, remove the ice water bath and stir. Overnight (13h),TLC (DCM:MeOH=100:1 and DCM:MeOH=10:1)Shows that the reaction is complete. Add water (200ml), mix, stand still, separate the layers, and extract the aqueous phase with dichloromethane (100+100ml).Combine the organic phases, wash with water (100ml), wash with citric acid solution (100ml),Wash with saturated sodium chloride (100ml), dry with anhydrous magnesium sulfate, filter with suction, and distill off the filtrate under reduced pressure.51.68g of yellow liquid was obtained. Silica gel column chromatography purification (DCM:PEDCM), 33.3g off-white solid was obtained, the yield was 62.5%.

References: [1]Tetrahedron,1997,vol. 53,p. 1391 - 1402.
[2]Patent: CN112759538,2021,A .Location in patent: Paragraph 0180-01883.
[3]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.

6
[ 7677-24-9 ]
[ 142009-99-2 ]
[ 422507-45-7 ]

References: [1]Synlett,1997,vol. 1997,p. 179 - 180.
[2]Organic Letters,2015,vol. 17,p. 568 - 571.

7
[ 7677-24-9 ]
[ 142009-99-2 ]
[ 187807-19-8 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.

8
[ 17853-42-8 ]
[ 142009-99-2 ]
4-[N-benzyl-N-(2-bromo-3-methyl-2-butenyl)amino]cyclohexanone [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

9
1,2-dibromo-2-butene [ No CAS ]
[ 142009-99-2 ]
[ 583887-17-6 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

10
[ 85970-82-7 ]
[ 142009-99-2 ]
[ 290301-57-4 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

11
[ 133834-87-4 ]
[ 142009-99-2 ]
[ 290301-49-4 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

12
[ 147644-04-0 ]
[ 142009-99-2 ]
[ 583887-16-5 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

13
[ 142009-99-2 ]
[ 178877-39-9 ]
[ 290301-46-1 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

14
[ 142009-99-2 ]
[ 222421-23-0 ]
4-[N-benzyl-N-(Z)-(3-iodo-2-methyl-2-propenyl)amino]cyclohexanone [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 1646 - 1650.

15
4-(benzylimino)cyclohexanone [ No CAS ]
[ 142009-99-2 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 14293 - 14305.

16
[ 62-53-3 ]
[ 142009-99-2 ]
N-benzyl-4-phenylimino-1-cyclohexylamine [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 14293 - 14305.

17
[ 142009-99-2 ]
2-benzyl-4-methyl-2-azabicyclo[4.3.1]dec-4-en-7-one [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 1646 - 1650.

18
[ 142009-99-2 ]
4-[benzyl-(2-methyl-allyl)-amino]-cyclohexanone [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2004,vol. 346,p. 1646 - 1650.

19
[ 142009-99-2 ]
2-benzyl-2-azabicyclo[4.3.1]dec-4-en-7-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

20
[ 142009-99-2 ]
2-benzyl-4-ethyl-2-azabicyclo[3.3.1]non-3-en-6-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

21
[ 142009-99-2 ]
[ 290301-47-2 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

22
[ 142009-99-2 ]
4-(N-benzyl-N-propargylamino)cyclohexanone [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

23
[ 142009-99-2 ]
2-benzyl-4-methylene-2-azabicyclo[3.3.1]nonan-6-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

24
[ 142009-99-2 ]
2-benzyl-4-[(E)-ethylidene]-2-azabicyclo[3.3.1]nonan-6-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.
[2]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

25
[ 142009-99-2 ]
4-(N-benzyl-N-but-2-ynyl)cyclohexanone [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5746 - 5749.

26
[ 142009-99-2 ]
[ 187807-20-1 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[2]Synlett,1997,vol. 1997,p. 179 - 180.

27
[ 142009-99-2 ]
[ 422506-79-4 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[2]Synlett,1997,vol. 1997,p. 179 - 180.

28
[ 142009-99-2 ]
[ 422507-26-4 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[2]Synlett,1997,vol. 1997,p. 179 - 180.

29
[ 142009-99-2 ]
[ 187807-27-8 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[2]Synlett,1997,vol. 1997,p. 179 - 180.

30
[ 142009-99-2 ]
(1RS,2SR,5RS)-6-benzyl-6-azabicyclo[3.2.1]octane-2-carbonitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[2]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[3]Synlett,1997,vol. 1997,p. 179 - 180.

31
[ 142009-99-2 ]
(1RS,2RS,5RS)-6-benzyl-6-azabicyclo[3.2.1]octane-2-carbonitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[2]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[3]Synlett,1997,vol. 1997,p. 179 - 180.

32
[ 142009-99-2 ]
(1RS,6RS,7SR)-2-benzyl-5-oxo-2-azabicyclo[4.3.1]decane-7-carbonitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[2]Synlett,1997,vol. 1997,p. 179 - 180.

33
[ 142009-99-2 ]
(1RS,6RS,7RS)-2-benzyl-5-oxo-2-azabicyclo[4.3.1]decane-7-carbonitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.
[2]Synlett,1997,vol. 1997,p. 179 - 180.

34
[ 142009-99-2 ]
[ 422507-39-9 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.

35
[ 142009-99-2 ]
N-benzyl-N-carboxymethyl-N-[4-cyanocyclohex-3-en-1-yl]ammonium chloride [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 2323 - 2328.

36
[ 4746-97-8 ]
[ 142009-99-2 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.
[2]Tetrahedron,1997,vol. 53,p. 1391 - 1402.
[3]Journal of Organic Chemistry,1995,vol. 60,p. 8089 - 8092.
[4]Tetrahedron Letters,1995,vol. 36,p. 1709 - 1712.
[5]Organic Letters,2015,vol. 17,p. 568 - 571.
[6]Chemical Communications,2019,vol. 55,p. 8816 - 8819.
[7]Patent: CN112759538,2021,A .

37
[ 142009-99-2 ]
[ 192373-28-7 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.

38
[ 142009-99-2 ]
C₂₂H₃₆N₂O₄Si [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.

39
[ 142009-99-2 ]
Benzyl-(2,4-dioxo-1,3-diaza-spiro[4.5]dec-8-yl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.

40
[ 142009-99-2 ]
4-(Benzyl-tert-butoxycarbonyl-amino)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclohexanecarboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.

41
[ 142009-99-2 ]
[ 192373-17-4 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.

42
[ 142009-99-2 ]
C₃₇H₄₆N₂O₆Si [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.

43
[ 100-46-9 ]
chloride of/the/ 2-nitro-toluene-sulfonic acid-⁽⁴⁾ [ No CAS ]
[ 142009-99-2 ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 4013 - 4016.
[2]Tetrahedron,1997,vol. 53,p. 1391 - 1402.

44
[ 142009-99-2 ]
[ 187807-23-4 ]

References: [1]Synlett,1997,vol. 1997,p. 179 - 180.

45
[ 142009-99-2 ]
[ 187807-19-8 ]

References: [1]Synlett,1997,vol. 1997,p. 179 - 180.
[2]Organic Letters,2015,vol. 17,p. 568 - 571.

46
[ 142009-99-2 ]
4-(N-benzyl-N-methylamino)-1-cyclohexene [ No CAS ]

References: [1]Synlett,1997,vol. 1997,p. 179 - 180.

47
[ 142009-99-2 ]
[ 422507-12-8 ]

References: [1]Synlett,1997,vol. 1997,p. 179 - 180.

48
[ 142009-99-2 ]
[ 187807-24-5 ]

References: [1]Synlett,1997,vol. 1997,p. 179 - 180.

49
[ 142009-99-2 ]
[ 188562-95-0 ]

References: [1]Tetrahedron,1997,vol. 53,p. 1391 - 1402.

50
[ 142009-99-2 ]
5-(Benzyl-tert-butoxycarbonyl-amino)-cyclohex-1-enecarboxylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 1391 - 1402.

51
[ 142009-99-2 ]
[ 188562-97-2 ]

References: [1]Tetrahedron,1997,vol. 53,p. 1391 - 1402.

52
[ 142009-99-2 ]
[ 188562-93-8 ]

References: [1]Tetrahedron,1997,vol. 53,p. 1391 - 1402.

53
[ 142009-99-2 ]
4-benzylamino-1-cyclohexenecarbonitrile trifluoroacetate [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 1391 - 1402.

54
[ 142009-99-2 ]
4-Benzylamino-cyclohex-1-enecarboxylic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 1391 - 1402.

55
[ 142009-99-2 ]
2-(7-Benzyl-7-aza-bicyclo[2.2.1]hept-1-yl)-ethanol [ No CAS ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 8089 - 8092.
[2]Journal of Organic Chemistry,1995,vol. 60,p. 8089 - 8092.

Historical Records

Technical Information

• Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 142009-99-2 ]

Aryls

A118656 [149506-79-6]

4-(Dibenzylamino)cyclohexanone

Similarity: 0.97

A228954 [1416352-02-7]

4-(Dibenzylamino)cyclohexanone hydrochloride

Similarity: 0.95

A186693 [2291-58-9]

9-Benzyl-9-azabicyclo[3.3.1]nonan-3-one

Similarity: 0.90

A300130 [32941-09-6]

1-Benzyl-2,6-dimethylpiperidin-4-one

Similarity: 0.90

A115124 [203661-73-8]

1-Benzyl-2-methylpiperidin-4-one

Similarity: 0.90

Ketones

A118656 [149506-79-6]

4-(Dibenzylamino)cyclohexanone

Similarity: 0.97

A228954 [1416352-02-7]

4-(Dibenzylamino)cyclohexanone hydrochloride

Similarity: 0.95

A186693 [2291-58-9]

9-Benzyl-9-azabicyclo[3.3.1]nonan-3-one

Similarity: 0.90

A300130 [32941-09-6]

1-Benzyl-2,6-dimethylpiperidin-4-one

Similarity: 0.90

A115124 [203661-73-8]

1-Benzyl-2-methylpiperidin-4-one

Similarity: 0.90

Amines

A118656 [149506-79-6]

4-(Dibenzylamino)cyclohexanone

Similarity: 0.97

A228954 [1416352-02-7]

4-(Dibenzylamino)cyclohexanone hydrochloride

Similarity: 0.95

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P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 142009-99-2

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