Home Cart 0 Sign in  
X

[ CAS No. 5570-78-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 5570-78-5
Chemical Structure| 5570-78-5
Chemical Structure| 5570-78-5
Structure of 5570-78-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 5570-78-5 ]

Related Doc. of [ 5570-78-5 ]

Alternatived Products of [ 5570-78-5 ]

Product Details of [ 5570-78-5 ]

CAS No. :5570-78-5 MDL No. :MFCD00101977
Formula : C8H17NO Boiling Point : -
Linear Structure Formula :- InChI Key :UZRXHHMTKCJKTQ-UHFFFAOYSA-N
M.W : 143.23 Pubchem ID :79681
Synonyms :

Calculated chemistry of [ 5570-78-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.43
TPSA : 23.47 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 0.93
Log Po/w (WLOGP) : 0.47
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 0.92
Consensus Log Po/w : 1.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.25
Solubility : 8.09 mg/ml ; 0.0565 mol/l
Class : Very soluble
Log S (Ali) : -1.01
Solubility : 14.0 mg/ml ; 0.0979 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.6
Solubility : 36.2 mg/ml ; 0.253 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.14

Safety of [ 5570-78-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5570-78-5 ]

* 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 [ 5570-78-5 ]
  • Downstream synthetic route of [ 5570-78-5 ]

[ 5570-78-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 5382-16-1 ]
  • [ 67-64-1 ]
  • [ 5570-78-5 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With acetic acid In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20 - 40℃; for 2.75 h;
Stage #3: With ammonia In water for 0.5 h;
A mixture of 4-hydroxypiperidine (10g, 0.10mol), acetone (21.8mL, 0.30mol), acetic acid (5.7mL, 0.10mol) and tetrahydrofuran (150mL) was stirred in an ice bath for 15 minutes.
Sodium triacetoxyborohydride (31.3g, 0.15mol) was then added portionwise and the mixture was stirred for a further 10 minutes.
The reaction mixture was then warmed and stirred at room temperature for 10 minutes and at 40°C for 2.5 hours.
The solvent was evaporated under reduced pressure and the residue was dissolved in water (50mL).
The aqueous solution was basified to pH9 with 0.88 ammonia and the solution was stirred for 30 minutes.
The reaction mixture was then extracted with diethyl ether (2x200mL) and the combined extracts were dried over sodium sulfate and concentrated in vacuo to give a yellow oil.
The oil was purified by column chromatography on silica gel, eluding with dichloromethane:methanol:0.88 ammonia, 96:4:1 to 90:10:1, to afford the title product as a yellow oil in quantitative yield, 14.6g.
1H-NMR(CDCl3, 400MHz) δ: 0.92-1.02(m, 6H), 1.41-1.57(m, 2H), 1.77-1.89(m, 2H), 2.07-2.23(m, 2H), 2.57-2.78(m, 3H), 3.43-3.85(brm, 2H)
MS ES+ m/z 144 [MH]+
100%
Stage #1: With acetic acid In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20 - 40℃; for 2.83333 h;
Stage #3: for 0.5 h;
Preparation 3 1 -lsopropyl-piperidin-4-olA mixture of 4-hydroxypiperidine (1Og, O.IOmol), acetone (21.8ml, 0.30mol), acetic acid (5.7ml, O.IOmol) and tetrahydrofuran (150ml) was stirred in an ice bath for 15 minutes. Sodium triacetoxyborohydride (31.3g, 0.15mol) was then added portion wise and the mixture was stirred for a further 10 minutes. The reaction mixture was then warmed and stirred at room temperature for 10 minutes and at 400C for 2.5 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in water (50ml). The aqueous solution was basified to pH9 with 0.88 ammonia and the solution was stirred for 30 minutes. The reaction mixture was then extracted with diethyl ether (2x200ml) and the combined extracts were dried over sodium sulfate and concentrated in vacuo to give a yellow oil. The oil was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 96:4:1 to 90:10:1 , to afford the title product as a yellow oil in quantitative yield, 14.6g.1HNMR(CDCI3, 400MHz) δ: 0.92-1.02(m, 6H), 1.41-1.57(m, 2H), 1.77-1.89(m, 2H), 2.07-2.23(m, 2H), 2.57-2.78(m, 3H), 3.43-3.85(brm, 2H) MS ES+ m/z 144 [MH]+
29%
Stage #1: With acetic acid In 1,2-dichloro-ethane at 20℃; for 12 h; Inert atmosphere
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 12 h;
To a stirred solution of piperidin-4-ol (1 g, 9.87 mmol) in DCE (100 ml) under an atmosphere of nitrogen was added acetic acid (1.78 g, 29.7 mmol) and acetone (5.72 g, 98.7 mmol). The reaction mixture was stirred for 12 h at RT before addition of STAB (6.29 g, 29.7 mmol).After stirring for 12 h at RT the reaction mixture was concentrated at reduced pressure to give a white solid. Purification by FCC [SiO2, eluting on a gradient from 98:2 EtOAc/MeOH to90:10:1 EtOAc/MeOH/NH3] to give the title compound (412 mg, 29 percent) as a colourless oil.1H NMR (250 MHz, CHLOROFORM-J) δ ppm 4.97 (1 H, br. s.), 3.39 (1 H, m, J=8.6, 4.0Hz), 2.23 - 2.77 (3 H, m), 1.88 - 2.16 (2 H, m), 1.49 - 1.75 (2 H, m), 1.35 (2 H, m, J=12.6,9.3, 9.3, 3.6 Hz), 0.63 - 0.97 (6 H, m).
Reference: [1] Patent: EP1595881, 2005, A1, . Location in patent: Page/Page column 64
[2] Patent: WO2007/52124, 2007, A1, . Location in patent: Page/Page column 17
[3] Patent: WO2009/121812, 2009, A1, . Location in patent: Page/Page column 69
[4] Patent: US2009/233910, 2009, A1, . Location in patent: Page/Page column 57
  • 2
  • [ 5382-16-1 ]
  • [ 75-26-3 ]
  • [ 5570-78-5 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In methanolHeating / reflux Intermediate 21: Methanesulfonic acid 1-isopropyl-piperidin-4-yl ester [] Step 1:; 4-Hydroxypiperidine (2.13g, 21.1mmol), K2CO3 (5.83g, 2eq.), 2-bromopropane (11.2g, 91 mmol, 4.3eq.) and MeOH (21.3ml) were refluxed together overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (40ml) and extracted with TBME (40ml). The aqueous phase was basified to pH 14 with 2M NaOH solution and extracted with DCM (9 x 50ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give 1-isopropyl-4-hydroxypiperidine (2.41g, 80percentth) as a pale yellow oil.1H NMR (400MHz, CDCl3) δ3.67 (m, 1H), 2.85-2.66 (m, 3H), 2.33-2.20 (m, 2H), 1.99-1.38 (m, 5H), 1.04 (d, 6H).
35% With potassium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12 h; In a similar fashion (Rl, GP A) 2-bromopropane (1.46 g, 11.86 mmol), gave the title compound (0.5 g, 35percent yield) as oil after purification by FCC [SiO2, eluting with 85:15:2 DCM / MeOH / NH3].1H NMR (250 MHz, CHLOROFORM-J) δ ppm 4.97 (1 H, br. s.), 3.39 (1 H, m, J=8.6, 4.0 Hz), 2.23 - 2.77 (3 H, m), 1.88 - 2.16 (2 H, m), 1.49 - 1.75 (2 H, m), 1.35 (2 H, m, J=12.6, 9.3, 9.3, 3.6 Hz), 0.63 - 0.97 (6 H, m).
2.2 g With potassium carbonate In methanol for 12 h; Reflux 4-piperidinol (2.13 g, 21.1 mmol) was added to methanol (21 mL), and potassium carbonate (5.83 g, 42.2 mmol) and 2-bromopropane (11.2 g, 90.7 mmol) were further added thereto, followed by refluxing for 12 hours while stirring. Then, the reaction mixture was mixed with 2M HCl (40 mL) and extracted three times with dichloromethane (50 mL). The organic layer thus obtained was dried over anhydrous magnesium sulfate, and filtered and distilled under reduced pressure to obtain the title compound (2.2 g) as oil. [0331] 1H NMR (300 MHz, CDCl3): δ 3.65 (m, 1H), 2.76 (m, 2H), 2.26 (m, 3H), 1.92 (m, 2H), 1.56 (m, 2H), 1.02 (d, 6H).
Reference: [1] Patent: EP1593679, 2005, A1, . Location in patent: Page/Page column 39
[2] Patent: WO2009/121812, 2009, A1, . Location in patent: Page/Page column 66
[3] Patent: WO2012/93809, 2012, A2, . Location in patent: Page/Page column 48-49
[4] Patent: US2013/274268, 2013, A1, . Location in patent: Paragraph 0329-0331
  • 3
  • [ 5355-68-0 ]
  • [ 5570-78-5 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With sodium tetrahydroborate In ethanol at 0 - 20℃;
Stage #2: With sodium hydroxide; water In dichloromethane at 0℃; for 4 h;
To a cold (0° C.) solution of 1-isopropylpiperidone (purchased at Chemie Brunschwig AG, 100 g, 1.0 eq.) in ethanol (500 mL) was added sodium borohydride (19.3 g, 0.7 eq.) in small portions.
The reaction mixture was allowed to warm up to room temperature and was stirred overnight.
After concentration in vacuo, ice water (1 kg), sodium hydroxide aqueous solution (28percent in mass, 0.5 L) and dichloromethane (1 L) were added.
The mixture was stirred vigorously for 4 h and the aqueous layer was extracted with dichloromethane.
Combined organic layers were washed with brine, dried over sodium sulfate, filtered and purified by fractionated vacuum distillation (20 mBar).
One fraction (95° C. at 20 mBar) was isolated to yield 61.3 g (60percent) of the title product as colorless oil. MS (m/e): 144.5 (MH+, 100percent).
60%
Stage #1: With sodium tetrahydroborate In ethanol at 20℃;
Stage #2: With sodium hydroxide; water In dichloromethane at 0℃; for 4 h;
To a cold solution of 1-isopropylpiperidone (purchased at Chemie Brunschwig AG, 100 g, 1.0 eq.) in ethanol (500 mL) was added sodium borohydride (19.3 g, 0.7 eq.) in small portions.
The reaction mixture was allowed to warm up to room temperature and was stirred overnight.
After concentrating the mixture in vacuo, ice water (1 kg), sodium hydroxide aqueous solution (28percent in mass, 0.5 L) and dichloromethane (1 L) were added.
The mixture was stirred vigorously for 4 h and the aqueous layer was extracted with dichloromethane.
Combined organic layers were washed with brine, dried over sodium sulfate, filtered and purified by fractionated vacuum distillation (20 mbar).
One fraction (boiling point 95° C. at 20 mBar) was isolated to yield 61.3 g (60percent) of the desired product as colorless oil. MS (m/e): 144.5 (MH+, 100percent).
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2229 - 2238
[2] Patent: US2007/123526, 2007, A1, . Location in patent: Page/Page column 13
[3] Patent: US2007/123515, 2007, A1, . Location in patent: Page/Page column 18-19
[4] Patent: US2767190, 1950, ,
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 1826
[6] Heterocycles, 1984, vol. 22, # 4, p. 749 - 761
  • 4
  • [ 16217-23-5 ]
  • [ 5570-78-5 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 1826
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 5570-78-5 ]

Alcohols

Chemical Structure| 106-52-5

[ 106-52-5 ]

1-Methylpiperidin-4-ol

Similarity: 0.92

Chemical Structure| 3518-83-0

[ 3518-83-0 ]

N-Ethyl-4-hydroxypiperidine

Similarity: 0.92

Chemical Structure| 5382-16-1

[ 5382-16-1 ]

4-Piperidinol

Similarity: 0.84

Chemical Structure| 104-58-5

[ 104-58-5 ]

3-(Piperidin-1-yl)propan-1-ol

Similarity: 0.84

Chemical Structure| 2403-89-6

[ 2403-89-6 ]

1,2,2,6,6-Pentamethylpiperidin-4-ol

Similarity: 0.83

Related Parent Nucleus of
[ 5570-78-5 ]

Aliphatic Heterocycles

Chemical Structure| 106-52-5

[ 106-52-5 ]

1-Methylpiperidin-4-ol

Similarity: 0.92

Chemical Structure| 3518-83-0

[ 3518-83-0 ]

N-Ethyl-4-hydroxypiperidine

Similarity: 0.92

Chemical Structure| 5382-16-1

[ 5382-16-1 ]

4-Piperidinol

Similarity: 0.84

Chemical Structure| 104-58-5

[ 104-58-5 ]

3-(Piperidin-1-yl)propan-1-ol

Similarity: 0.84

Chemical Structure| 2403-89-6

[ 2403-89-6 ]

1,2,2,6,6-Pentamethylpiperidin-4-ol

Similarity: 0.83

Piperidines

Chemical Structure| 106-52-5

[ 106-52-5 ]

1-Methylpiperidin-4-ol

Similarity: 0.92

Chemical Structure| 3518-83-0

[ 3518-83-0 ]

N-Ethyl-4-hydroxypiperidine

Similarity: 0.92

Chemical Structure| 5382-16-1

[ 5382-16-1 ]

4-Piperidinol

Similarity: 0.84

Chemical Structure| 104-58-5

[ 104-58-5 ]

3-(Piperidin-1-yl)propan-1-ol

Similarity: 0.84

Chemical Structure| 2403-89-6

[ 2403-89-6 ]

1,2,2,6,6-Pentamethylpiperidin-4-ol

Similarity: 0.83