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[ CAS No. 147539-41-1 ] {[proInfo.proName]}

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Chemical Structure| 147539-41-1
Chemical Structure| 147539-41-1
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Product Details of [ 147539-41-1 ]

CAS No. :147539-41-1 MDL No. :MFCD02259411
Formula : C11H22N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CZYUGTLMFHDODF-UHFFFAOYSA-N
M.W : 214.30 Pubchem ID :15380702
Synonyms :

Calculated chemistry of [ 147539-41-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.91
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 64.2
TPSA : 41.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.87
Log Po/w (XLOGP3) : 1.24
Log Po/w (WLOGP) : 1.22
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 0.76
Consensus Log Po/w : 1.45

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.69
Solubility : 4.42 mg/ml ; 0.0206 mol/l
Class : Very soluble
Log S (Ali) : -1.71
Solubility : 4.17 mg/ml ; 0.0195 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.72
Solubility : 4.08 mg/ml ; 0.0191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.24

Safety of [ 147539-41-1 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 147539-41-1 ]

* 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.

  • Upstream synthesis route of [ 147539-41-1 ]
  • Downstream synthetic route of [ 147539-41-1 ]

[ 147539-41-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 79099-07-3 ]
  • [ 74-89-5 ]
  • [ 147539-41-1 ]
YieldReaction ConditionsOperation in experiment
99% With formic acid; palladium 10% on activated carbon; hydrogen In ethanol at 50℃; Autoclave To a suspension of N-(tert-butoxycarbonyl)-4-piperidone (10.00 g, 50.19 mmol) in EtOH (75 mL) was added 10percent Pd/C (1.00 g, 10percent wt.), NH3Me (33percent in ethanol, 27 mL, 0.20 mol) and HCOOH (46 mg, 1.00 mmol). The reaction mixture was sealed into an autoclave under 4 MPa H2atmosphere and stirred at 50 °C overnight, then cooled to room temperature and filtered. The filtrate was concentrated in vacuo to give the title compound as light yellow liquid (10.70 g, 99percent>).MS (ESI, pos. ion) m/z: 215.3 [M+H]+;'H NMR (400 MHz, CDC13): δ (ppm) 4.01 (m, 2H), 2.79 (m, 2H), 2.48 (m, 1H), 2.42 (s, 3H), 1.83 (m, 2H), 1.44 (s, 9H), 1.28-1.15 (m, 2H).
99% With formic acid; palladium 10% on activated carbon; hydrogen In ethanol at 50℃; Autoclave N- (tert-Butoxycarbonyl) -4-Piperidone (10.00 g, 50.19 mmol)Was added to anhydrous ethanol, and 10percent Pd / C (1.00 g, 10percent wt.) Was added thereto,Methylamine in ethanol (33percent, 27 mL, 0.20 mol)And formic acid (46 mg, 1.00 mmol) were added and the mixture sealed in a 4 MPa hydrogen autoclave and stirred overnight at 50 ° C. The system was returned to room temperature and filtered. The filtrate was concentrated under reduced pressure to give the title compound as a pale yellow liquid (10.70 g 99percent).
98% With hydrogen In ethanol at 20℃; for 18 h; Preparation 52: tert-Butyl 4-(methylamino)piperidine-1-carboxylate 10percent Pd/C (2 g) was added to a solution of tert-butyl 4-oxopiperidine-1-carboxylate (20 g, 100 mmol) in methylamine (33percent in ethanol, 10 mL) and the mixture was stirred at room temperature, under 60 psi of hydrogen, for 18 hours. The reaction mixture was then filtered through Arbocel.(R). and the filtrate was concentrated in vacuo. The residue was azeotroped with dichloromethane (.x.3) and the dried under vacuum for 72 hours to afford the title compound as a solid in 98percent yield, 21.1 g. LRMS APCI m/z 215 [M+H]+
97% With palladium 10% on activated carbon; hydrogen In methanol for 24 h; To a solution of 1-Boc-4-piperidone (500 mg, 2.51 mmol) in methanol (20 mL), were sequentially added 40percent solution of methylamine in methanol (0.90 mL, 8.78 mmol), and 10percent palladium on carbon (50 mg). The reaction mixture placed under an atmosphere of hydrogen for 24 h. The reaction mixture was then purged with nitrogen and filtered through a pad of Celite, which was then washed with methanol. The filtrate was concentrated in vacuo to afford tert butyl4-(methylamino)piperidine-1-carboxylate (4) (520 mg, 97percent).
93.5% With hydrogen In methanol for 72 h; 1-TERT-BUTOXYCARBONYLPIPERID-4-ONE (6.18 g, 31 mmol) was dissolved in a 2.0 M solution of methylamine in methanol (56 mL, 112 mmol). This solution was added to 10percent palladium on carbon (wet, 1.3 g) and the mixture placed under an atmosphere of hydrogen for 72 h. The reaction mixture was then purged with nitrogen and filtered through a pad of Celite, which was then washed with methanol. The resulting hazy filtrate was filtered through a 0. 2, UM filter and then concentrated in vacuo to afford the title intermediate (6.16 g, 29 mmol, 93.5percent yield).
93% With palladium 10% on activated carbon In methanol; water at 50℃; for 1 h; Inert atmosphere tert-Butyl 4-(methylamino)piperidine-1-carboxylate A solution of methanamine (38.0 mL, 442 mmol, 40percent aqueous solution) in methanol(100 mL) was added to wet palladium (1.602 g, 1.506 mmol, 10percent on activatedcharcoal) at room temperature under an atmosphere of argon. To this mixture wasadded tert-butyl 4-oxopiperidine-l-carboxylate (20 g, 100 mmol) portionwise and themixture was allowed to stir at 50 °C, 20 bar over lh. The suspension was flushed with argon and was filtered through celite and the celite was washed with DCM. The filtrate was evaporated in vacuum to give the product as a clear oil. The oil was- dissolved in EtOAc and was washed with water. The organic layer was dried (MgSO4)and evaporated in vacuum to give a clear oil. Used without further purification. tertl3utyl 4-(methylamino)piperidine- 1 -carboxylate (20 g, 93 percent yield).
93% With palladium 10% on activated carbon; hydrogen In methanol; water at 50℃; for 2 h; To a well purged solution of tert-butyl 4-oxopiperidine-l -carboxylate (20 g, 100 mmol) in methanol (100 mL) and methanamine (40percent in water) (38.0 mL, 442 mmol) was added palladium (10 wtpercent on activated charcoal) (1.602 g, 1.506 mmol) and placed in Parr reactor. The reaction mixture was allowed to stir under H2 atmosphere (20 atm) at 50 °C for 2h. The reaction was then allowed to slowly cool down to room temperature, purged with N2 and filtered. Evaporation of the filtrate afforded tert-butyl 4-(methylamino)piperidine-l -carboxylate as yellowish oil (20 g, 93percent yield).
80% With sodium cyanoborohydride In methanol at 0 - 25℃; for 14 h; Molecular sieve To a solution of 1 ,1-dimethylethyl 4-oxo-1 -piperidinecarboxylate (5.25 g, 0.026 mol) in MeOH (50 mL) at O0C were added methylamine (0.81 g, 0.026 mol), activated molecular sieve and NaCNBH4 (1.63 g, 0.026 mmol). The mixture was warmed up to 25°C gradually. After stirring for 14 hr, the mixture was filtered and diluted with water. MeOH was removed to generate a brown residue which was re-dissolved in NaHCO3 solution. The aqueous solution was extracted several times with DCM. The organic fractions were combined, concentrated and purified with column chromatppgraphy (0-10percent MeOH in DCM (1percent NH4OH)) to provide the desired product as a colorless oil (4.5 g, 80percent): LC/MS (ES) m/e 215 (M+H)+
72% With palladium 10% on activated carbon; hydrogen In methanol; water at 50℃; for 2 h; Inert atmosphere; Autoclave In a 250 mL flask was placed tert-butyl 4-oxopiperidine-l-carboxylate (20 g, 100 mmol) in methanol (100 mL), at room temperature under inert atmosphere, to give a colorless solution. Methanamine (40percent in water) (38 mL, 441 mmol) was added, followed by palladium (10percent on charcoal, 1.709 g, 1.606 mmol). The reaction flask was placed in an autoclave and was charged with 20 bar of hydrogen. The autoclave was heated at 50°C and stirred for 2 h. The reaction mixture was cooled slowly, filtered through celite, and the solvent was evaporated. The crude product was dissolved in water and the aqueous mixture was extracted with ethyl acetate. The organics were dried over MgS04and concentrated to yield a pale yellow oil. (Yield: 16.27 g, 72percent).
55%
Stage #1: With titanium(IV) isopropylate In ethanol at 20℃; for 5 h;
Stage #2: With sodium tetrahydroborate In ethanol for 2 h;
3.8 mL (13 mmol) of titanium isopropoxide and 2 g (10 mmol) of 1-tert-butoxycarbonyl-piperidin-4-one are added to 3.7 mL (30 mmol) of a 33percent solution of methylamine in ethanol.
The solution is stirred for 5 hours at room temperature then 378 mg (10 mmol) of sodium borohydride is added.
Stirring is continued for a further 2 hours then 2 mL of water is added.
The reaction mixture is filtered then the solvents are evaporated to give 1.18 g (55percent) of 4-methylamino-1-tert-butoxycarbonyl-piperidine in the form of an oil.

Reference: [1] Patent: WO2015/73267, 2015, A1, . Location in patent: Paragraph 332
[2] Patent: CN104650092, 2017, B, . Location in patent: Paragraph 0533-0536
[3] Patent: US2006/160786, 2006, A1, . Location in patent: Page/Page column 32
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 17, p. 4281 - 4285
[5] Patent: WO2005/7645, 2005, A1, . Location in patent: Page 77
[6] Patent: WO2015/12708, 2015, A1, . Location in patent: Page/Page column 14; 15; 16
[7] Patent: WO2015/16729, 2015, A1, . Location in patent: Page/Page column 34
[8] Patent: WO2007/16610, 2007, A2, . Location in patent: Page/Page column 62
[9] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 4, p. 1084 - 1088
[10] Patent: WO2015/16728, 2015, A1, . Location in patent: Page/Page column 35
[11] Patent: US2009/42876, 2009, A1, . Location in patent: Page/Page column 28-29
[12] Patent: WO2003/89412, 2003, A1, . Location in patent: Page/Page column 22
[13] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 336 - 343
[14] Patent: WO2009/53716, 2009, A1, . Location in patent: Page/Page column 101
[15] Patent: WO2005/70940, 2005, A2, . Location in patent: Page/Page column 71
[16] Patent: WO2005/70941, 2005, A1, . Location in patent: Page/Page column 40
[17] Patent: US2007/149512, 2007, A1, . Location in patent: Page/Page column 21
[18] Patent: WO2013/173720, 2013, A1, . Location in patent: Page/Page column 130
  • 2
  • [ 191212-86-9 ]
  • [ 147539-41-1 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogen In methanol at 50℃; ll.2.b4-Methylamino-piperidine-1-carboxylic acid te/f-butyl esterA mixture of 4.5 g (14.78 mmol) 4-(benzyl-methyl-amino)-piperidine-1-carboxylic acid te/f- butyl ester and 1 g of Pd/C (10percent) in 100 ml of methanol is hydrogenated at 500C and 5 bar.The reaction mixture is filtered and the filtrate concentrated.Yield: 2.95 g (93percent of theory),EII Mass spectrum: m/z = 215 [M+H]+
Reference: [1] Patent: WO2008/71646, 2008, A1, . Location in patent: Page/Page column 78
  • 3
  • [ 593-51-1 ]
  • [ 79099-07-3 ]
  • [ 147539-41-1 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: at 20℃; for 2 h;
Stage #2: With sodium cyanoborohydride In methanol at 0 - 20℃; for 14 h;
1-(6-Methoxypyridin-3-yl)-N-methylpiperidin-4-amine (AMN-51)
Stage 1: tert-Butyl 4-(methylamino)piperidine-1-carboxylat
tert-Butyl 4-oxopiperidine-1-carboxylate (5.0 g, 25.126 mmol, 1.0 eq.) was dissolved in MeOH (50 ml); AcOH (2 drops) and CH3NH2.HCl (2.2 g, 32.663 mmol, 1,3 eq.) were added and stirring was carried out for 2 hours at RT. NaCNBH3 (3.11 g, 50.25 mmol, 2.0 eq.) was added in portions at 0° C. and the mixture was stirred for 14 hours at RT.
The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography (Alox, 3percent MeOH in DCM). Yield: 55percent (3.0 g, 14.019 mmol)
Reference: [1] Patent: US2012/71461, 2012, A1, . Location in patent: Page/Page column 140
[2] Patent: WO2006/46031, 2006, A1, . Location in patent: Page/Page column 63-64
[3] Patent: US2005/20623, 2005, A1, . Location in patent: Page 97-98
  • 4
  • [ 301220-70-2 ]
  • [ 147539-41-1 ]
Reference: [1] Patent: EP1847535, 2007, A1, . Location in patent: Page/Page column 37
  • 5
  • [ 847039-05-8 ]
  • [ 147539-41-1 ]
Reference: [1] Patent: WO2005/19194, 2005, A1, . Location in patent: Page/Page column 34-35
  • 6
  • [ 546-68-9 ]
  • [ 79099-07-3 ]
  • [ 147539-41-1 ]
YieldReaction ConditionsOperation in experiment
57% With aqueous ammonia; sodium borohydrid; methylamine hydrochloride; triethylamine In ethanol; water Reference Example 46
tert-butyl 4-(methylamino)piperidine-1-carboxylate
To tert-butyl 4-oxo-1-piperidinecarboxylate (3.99 g, 20 mmol) was added ethanol (30 ml), and methylamine hydrochloride (2.70 g, 40 mmol), triethylamine (5.6 ml, 40 mmol) and titanium(IV)isopropoxide (11.8 ml, 40 mmol) were added under ice-cooling with stirring, and the mixture was stirred at room temperature for 8 hr.
Then, to the reaction mixture was added sodium borohydride (1.14 g, 30 mmol), and the mixture was stirred at room temperature for 15 hr.
To the reaction mixture was added 28percent aqueous ammonia, and the reaction solution was filtered off through celite.
The filtrate was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with dichloromethane-ethanol=5:1 mixed solvent, and dried over anhydrous magnesium sulfate.
The insoluble material was filtered off, and the solution was concentrated under reduced pressure.
The obtained oil was purified by silica gel column chromatography (dichloromethane-methanol) to give the title compound (2.46 g, yield 57percent) as a pale-yellow oil.
1H-NMR (300 MHz, CDCl3); δ(ppm) 1.16-1.29 (m, 2H), 1.46 (s, 9H), 1.83-1.87 (m, 2H), 2.44 (s, 3H), 2.46-2.53 (m, 1H), 2.80 (t, J=11.7, 2H), 4.02-4.05 (m, 2H).
Reference: [1] Patent: US2012/196824, 2012, A1,
  • 7
  • [ 79099-07-3 ]
  • [ 147539-41-1 ]
Reference: [1] Patent: US2001/44435, 2001, A1,
[2] Patent: US6297269, 2001, B1,
[3] Patent: US5489593, 1996, A,
  • 8
  • [ 24424-99-5 ]
  • [ 7144-05-0 ]
  • [ 147539-41-1 ]
Reference: [1] Patent: US5561146, 1996, A,
  • 9
  • [ 79099-07-3 ]
  • [ 56553-60-7 ]
  • [ 107-06-2 ]
  • [ 147539-41-1 ]
Reference: [1] Patent: US6166006, 2000, A,
  • 10
  • [ 124-63-0 ]
  • [ 147539-41-1 ]
  • [ 70724-74-2 ]
Reference: [1] Patent: WO2009/53716, 2009, A1, . Location in patent: Page/Page column 101
[2] Patent: WO2009/47161, 2009, A1, . Location in patent: Page/Page column 140
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