[ CAS No. 187669-28-9 ] tert-Butyl 4-(piperazin-1-yl)benzoate

Cat. No.: A746556

2D 3D

Structure of 187669-28-9 * Storage: Keep in dark place,Sealed in dry,Room Temperature

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Quality Control of [ 187669-28-9 ]

COA NMR CNMR HPLC LC-MS

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Specification

Alternatived Products of [ 187669-28-9 ]

Product Details of [ 187669-28-9 ]

CAS No. :	187669-28-9	MDL No. :	MFCD09608130
Formula :	C₁₅H₂₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KROXQOZMVCDQGV-UHFFFAOYSA-N
M.W :	262.35	Pubchem ID :	23081213
Synonyms :

Safety of [ 187669-28-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 187669-28-9 ]

* 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 [ 187669-28-9 ]

[ 187669-28-9 ] Synthesis Path-Downstream 1~12

1
[ 110-85-0 ]
[ 58656-98-7 ]
[ 187669-28-9 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 8020 - 8022
[2]Synthesis,2008,p. 2398 - 2404

2
[ 50-00-0 ]
[ 187669-28-9 ]
[ 4255-62-3 ]
[ 1044598-92-6 ]

Reference： [1]Synthesis,2008,p. 2398 - 2404
[2]Chemical Communications,2010,vol. 46,p. 8020 - 8022

3
[ 187669-28-9 ]
4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)-3-methylphenyl)piperazin-1-yl)benzoic acid monohydrochloride [ No CAS ]

Reference： [1]Patent: WO2016/87878,2016,A1

4
[ 187669-28-9 ]
tert-butyl 4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)-tetrahydrofuran-3-yl)methoxy)-3-methylphenyl)piperazin-1-yl)benzoate [ No CAS ]

Reference： [1]Patent: WO2016/87878,2016,A1

5
[ 187669-28-9 ]
[ 2362-12-1 ]
tert-butyl 4-(4-(4-hydroxy-3-methylphenyl)piperazin-1-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II); lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at 15 - 25℃;Inert atmosphere;	A solution of te/f-butyl 4-(piperazin-1-yl)benzoate (Xb) (100 g, 381 mmol) and 4-bromo-2- methylphenol (85.5 g, 457 mmol) in anhydrous DMF (1.00 L) was degassed by placing the mixture alternately under vacuum and then a nitrogen atmosphere three times. Following this procedure, RuPhos G3 (6.38 g, 7.62 mmol) was added at 15-25C followed by a solution of □HMDS in THF (1.06 M, 432. mL, 457 mmol) over 5 min whilst maintaining the temperature within 15-30C, (water bath cooling). After stirring for 5 min additional aliquots of the solution of LiHMDS (1.06 M in THF) was added to the reaction mixture in fourteen equal portions (14 x 36 mL, total 504 mL, 533 mmol) at 2 min intervals, resulting in an exotherm from 16C- 21 C.The reaction was stirred at 15-25C overnight (at which point HPLC showed the formation of 72.% of the desired product) and the pH of the mixture was adjusted to 7.3 by the addition of 2M hydrochloric acid (-900 mL). The aq phase was separated and was extracted repeadtedly with EtOAc (1.0 L, 500 mL and 2 x 250 mL). The combined organics were washed with brine (6 x 400 mL), dried over MgS04 and concentrated in vacuo to give a sticky yellow solid. The solid so obtained was suspended in IPA (500 mL) and was stirred at 15-25C for 1 hr. The suspension was filtered and the filter cake was washed with IPA (250 mL, 200 mL) and pulled dry. Further drying of the product in vacuo at 50C provided the title compound, intermediate (Vlllb) as an off-white solid (105.6 g, 75%, HPLC purity 97.1 %); R' 12.23 min; m/z 369.3 (M+H)+ (ES+)

Reference： [1]Patent: WO2016/87878,2016,A1 .Location in patent: Page/Page column 28

6
[ 187669-28-9 ]
C₁₄H₁₉ClO [ No CAS ]
tert-butyl 4-(4-((2-(3-chlorobicyclo[1.1.1]pentan-1-yl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		To a stirred solution of Intermediate 36-8 (85 mg, 0.361 mmol) in EtOH (3 mL) was added tert- Butyl 4-(piperazin-l-yl)benzoate (104 mg, 0.397 mmol) and AcOH (cat.). After 15 min, the reaction was cooled to 0 C, treated with NaCNBfE (33.6 mg, 0.535 mmol) and warmed to rt. After 16 h, the reaction was diluted with sat. aq. NaHCCh and extracted with DCM (3 x 15 mL). The combined organic layers were dried over Na SCU, filtered and concentrated. The crude product was purified by column chromatography (S1O2, EtOAc/pet. ether) to obtain tert-Butyl 4-(4-((2-(3-chlorobicyclo[l.l.l]pentan-l-yl)-5,5- dimethylcyclohex-l-en-l-yl)methyl)piperazin-l-yl)benzoate (Intermediate 36-9) as a white solid (80 mg, 50% yield). LC/MS (ESI) m/z 485.6 [M+H]+.

Reference： [1]Patent: WO2019/139902,2019,A1 .Location in patent: Paragraph 0401

7
[ 187669-28-9 ]
(R)-4-(4-((2-(3-chlorobicyclo[1.1.1]pentan-1-yl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-N-((4-((4-morpholino-1-(phenylthio)butan-2-yl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2019/139902,2019,A1

8
[ 187669-28-9 ]
4-(4-((2-(3-chlorobicyclo[1.1.1]pentan-1-yl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoic acid [ No CAS ]

Reference： [1]Patent: WO2019/139902,2019,A1

9
[ 187669-28-9 ]
2-(3-chlorobicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-ene-1-carbaldehyde [ No CAS ]
tert-butyl 4-(4-((2-(3-chlorobicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%		To a stirred solution of 2-(3-chlorobicyclo[l.l.l]pentan-1-yl)-4,4- dimethylcyclohex-1-ene-1-carbaldehyde (700 mg, 2.94 mmol) in toluene (15 mL) was added <strong>[187669-28-9]tert-butyl 4-(piperazin-1-yl)benzoate</strong> (773 mg, 2.94 mmol) and titanium (IV) ethoxide (1.34 g, 5.88 mmol) at rt. After 2 h, the reaction mixture was cooled to 0 C and treated with Na(OAc)3BH (1.8 g, 8.82 mmol), warmed to rt and stirred for 16 h . The reaction was then concentrated and the residue was diluted with sat. aq. NaHCO3 (10 mL) and extracted with DCM (3 x 20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, EtOAc/pet. ether) to afford tert-butyl 4-(4-((2-(3-chlorobicyclo[l.l.l]pentan-1-yl)-4,4-dimethylcyclohex- l-en-1-yl)methyl)piperazin-1-yl)benzoate (Intermediate 48-1) as a white solid (540 mg, 38% yield). 1H NMR (400 MHz, CDCL) d 7.86 (d, J = 8.8 Hz, 2H), 6.84 (d, J = 9.2 Hz, 2H), 3.29-3.27 (m, 4H), 2.98 (s, 2H), 2.49-1.47 (m, 4H), 2.30 (s, 6H), 2.11-2.04 (m, 2H), 1.68 (s, 2H), 1.57 (s, 9H), 1.33-1.25 (m, 2H), 0.88 (s, 6H); LC/MS (ESI) m/z 485.4 [M+H]+.
38%		To a stirred solution of 2-(3-chlorobicyclo[l.l.l]pentan-1-yl)-4,4- dimethylcyclohex-1-ene-1-carbaldehyde (700 mg, 2.94 mmol) in toluene (15 mL) was added <strong>[187669-28-9]tert-butyl 4-(piperazin-1-yl)benzoate</strong> (773 mg, 2.94 mmol) and titanium (IV) ethoxide (1.34 g, 5.88 mmol) at rt. After 2 h, the reaction mixture was cooled to 0 C and treated with Na(OAc)3BH (1.8 g, 8.82 mmol), warmed to rt and stirred for 16 h . The reaction was then concentrated and the residue was diluted with sat. aq. NaHCO3 (10 mL) and extracted with DCM (3 x 20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, EtOAc/pet. ether) to afford tert-butyl 4-(4-((2-(3-chlorobicyclo[l.l.l]pentan-1-yl)-4,4-dimethylcyclohex- l-en-1-yl)methyl)piperazin-1-yl)benzoate (Intermediate 48-1) as a white solid (540 mg, 38% yield). 1H NMR (400 MHz, CDCL) d 7.86 (d, J = 8.8 Hz, 2H), 6.84 (d, J = 9.2 Hz, 2H), 3.29-3.27 (m, 4H), 2.98 (s, 2H), 2.49-1.47 (m, 4H), 2.30 (s, 6H), 2.11-2.04 (m, 2H), 1.68 (s, 2H), 1.57 (s, 9H), 1.33-1.25 (m, 2H), 0.88 (s, 6H); LC/MS (ESI) m/z 485.4 [M+H]+.

Reference： [1]Patent: WO2021/222114,2021,A1 .Location in patent: Paragraph 0300
[2]Patent: WO2021/222114,2021,A1 .Location in patent: Paragraph 0300

10
[ 187669-28-9 ]
2-(3-chlorobicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-ene-1-carbaldehyde [ No CAS ]
4-(4-((2-(3-chlorobicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoic acid [ No CAS ]

Reference： [1]Patent: WO2021/222114,2021,A1

11
[ 187669-28-9 ]
2-(3-fluorobicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-ene-1-carbaldehyde [ No CAS ]
ethyl 4-(4-((2-(3-fluorobicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		A stirred solution of 2-(3-fluorobicyclo[l.l.l]pentan-1-yl)-4,4- dimethylcyclohex-1-ene-1-carbaldehyde (1.2 g, 5.40 mmol) in toluene (15 mL) was treated with ethyl 4-(piperazin-1-yl)benzoate (1.26 g, 5.40 mmol) and titanium (IV) ethoxide (2.4 g, 10.81 mmol ) at rt and stirred for 2 h. The reaction mixture was then cooled to 0 C, and Na(OAc)3BH (3.4 g, 16.21 mmol) was added and the reaction was warmed to rt. After 16 h, the reaction was concentrated, diluted with sat. aq. NaHCO3(10 mL) and washed with DCM (3 x 25 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was column chromatography (SiO2, EtOAc/pet. ether) to afford ethyl 4-(4-((2-(3-fluorobicyclo[ 1.1.1 ]pentan- 1 -yl)-4,4-dimethylcyclohex- 1 -en- 1 - yl)methyl)piperazin-1-yl)benzoate (Intermediate 49-1) (1.3 g, 54% yield) as a white solid. 7.91 (d, J = 7.2 Hz, 2H), 6.85 (d, J = 7.2 Hz, 2H), 4.32 (q, J = 7.2 Hz, 2H), 3.31-3.29 (m, 4H), 3.00 (s, 2H), 2.50-2.47 (m, 4H), 2.21 (d, J = 2.4 Hz, 6H), 2.14-2.09 (m, 2H), 1.71 (s, 2H), 1.39-1.25 (m, 5H), 0.88 (s, 6H); LC/MS (ESI) m/z 441.7 [M+H]+.
54%		A stirred solution of 2-(3-fluorobicyclo[l.l.l]pentan-1-yl)-4,4- dimethylcyclohex-1-ene-1-carbaldehyde (1.2 g, 5.40 mmol) in toluene (15 mL) was treated with ethyl 4-(piperazin-1-yl)benzoate (1.26 g, 5.40 mmol) and titanium (IV) ethoxide (2.4 g, 10.81 mmol ) at rt and stirred for 2 h. The reaction mixture was then cooled to 0 C, and Na(OAc)3BH (3.4 g, 16.21 mmol) was added and the reaction was warmed to rt. After 16 h, the reaction was concentrated, diluted with sat. aq. NaHCO3(10 mL) and washed with DCM (3 x 25 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was column chromatography (SiO2, EtOAc/pet. ether) to afford ethyl 4-(4-((2-(3-fluorobicyclo[ 1.1.1 ]pentan- 1 -yl)-4,4-dimethylcyclohex- 1 -en- 1 - yl)methyl)piperazin-1-yl)benzoate (Intermediate 49-1) (1.3 g, 54% yield) as a white solid. 7.91 (d, J = 7.2 Hz, 2H), 6.85 (d, J = 7.2 Hz, 2H), 4.32 (q, J = 7.2 Hz, 2H), 3.31-3.29 (m, 4H), 3.00 (s, 2H), 2.50-2.47 (m, 4H), 2.21 (d, J = 2.4 Hz, 6H), 2.14-2.09 (m, 2H), 1.71 (s, 2H), 1.39-1.25 (m, 5H), 0.88 (s, 6H); LC/MS (ESI) m/z 441.7 [M+H]+.

Reference： [1]Patent: WO2021/222114,2021,A1 .Location in patent: Paragraph 0304
[2]Patent: WO2021/222114,2021,A1 .Location in patent: Paragraph 0304

12
[ 187669-28-9 ]
2-(3-fluorobicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-ene-1-carbaldehyde [ No CAS ]
4-(4-((2-(3-fluorobicyclo[1.1.1]pentan-1-yl)-4,4-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoic acid [ No CAS ]

Reference： [1]Patent: WO2021/222114,2021,A1

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Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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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

[ CAS No. 187669-28-9 ] tert-Butyl 4-(piperazin-1-yl)benzoate

Quality Control of [ 187669-28-9 ]

Related Doc. of [ 187669-28-9 ]

Product Details of [ 187669-28-9 ]

Safety of [ 187669-28-9 ]

Application In Synthesis of [ 187669-28-9 ]

[ 187669-28-9 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 187669-28-9 ]

Aryls

Esters

Related Parent Nucleus of [ 187669-28-9 ]

Piperazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 187669-28-9 ]

Related Parent Nucleus of
[ 187669-28-9 ]