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[ CAS No. 504-20-1 ] {[proInfo.proName]}

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Chemical Structure| 504-20-1
Chemical Structure| 504-20-1
Structure of 504-20-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 504-20-1 ]

CAS No. :504-20-1 MDL No. :MFCD00008901
Formula : C9H14O Boiling Point : -
Linear Structure Formula :- InChI Key :MTZWHHIREPJPTG-UHFFFAOYSA-N
M.W : 138.21 Pubchem ID :10438
Synonyms :

Calculated chemistry of [ 504-20-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.44
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.63
TPSA : 17.07 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) : -5.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 2.84
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 2.06
Consensus Log Po/w : 2.38

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.35
Solubility : 0.612 mg/ml ; 0.00443 mol/l
Class : Soluble
Log S (Ali) : -2.86
Solubility : 0.192 mg/ml ; 0.00139 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.53
Solubility : 4.1 mg/ml ; 0.0296 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.48

Safety of [ 504-20-1 ]

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 [ 504-20-1 ]

* 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 [ 504-20-1 ]
  • Downstream synthetic route of [ 504-20-1 ]

[ 504-20-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 504-20-1 ]
  • [ 36768-62-4 ]
YieldReaction ConditionsOperation in experiment
71% With ammonia; acetic acid In methanol EXAMPLE 3
100 ml of methanol, 150 ml of liquid ammonia, 1 ml of acetic acid and 20 g of a standard commercial hydrogenation catalyst (Raney cobalt), were introduced into a 0.7 litre capacity hydrogenation autoclave.
The autoclave was heated to the hydrogenation temperature of approximately 150°C under a hydrogen pressure of approximately 100 atms, after which a solution of 100 g of phorone in 100 ml of methanol was pumped in over a period of about 1 hour.
Hydrogenation was complete after about another hour.
After cooling, the autoclave was vented, the reaction solution filtered off from the catalyst and subjected to fractional distillation, yielding 80 g (71percent of the theoretical yield) of 4-amino-2,2,6,6-tetramethyl piperidine with a boiling point of 82°-88°C/15 Torr.
64% With acetic acid In methanol EXAMPLE 1
100 ml of methanol, 150 ml (approximately 6 moles) of liquid ammonia and 1 ml of acetic acid, together with 20 g of a standard hydrogenation catalyst (Raney cobalt), were introduced into a 0.7 litre capacity hydrogenation autoclave.
The autoclave was then heated to a temperature of approximately 110°C and the hydrogen pressure maintained in the range from 130 to 150 atms.
After the prescribed hydrogenation temperature of 110°C had been reached, a solution of 100 g (0.725 mol) of phorone in 100 ml of methanol was pumped in over a period of 1 hour.
Hydrogenation was over after about another hour.
After cooling, the autoclave was vented, the reaction solution filtered off from the catalyst and subjected to fractional distillation, yielding 72.5 g (64percent of the theoretical yield) of 4-amino-2,2,6,6-tetramethyl piperidine with a boiling point of 88°-92°C/16 Torr.
54% With ammonia; acetic acid In methanol EXAMPLE 2
100 ml of methanol, 150 ml of liquid ammonia, 1 ml of acetic acid and 20 g of a standard commercial hydrogenation catalyst (Raney nickel) were introduced into a 0.7 litre capacity autoclave.
The autoclave was heated to a hydrogenation temperature of 110°C under a hydrogen pressure of 130 to 150 atms, after which a solution of 100 g of phorone in 100 ml of methanol was pumped in over a period of approximately 1 hour.
Hydrogenation was over after about another hour.
After cooling, the autoclave was vented, the reaction solution filtered off from the catalyst and subjected to fractional distillation, yielding 61 g (54percent of the theoretical yield) of 4-amino-2,2,6,6-tetramethyl piperidine with a boiling point of 89°-95°C/18 Torr.
41.5% With ammonia; acetic acid In methanol EXAMPLE 6
100 ml of methanol, 110 ml of liquid ammonia, 1 ml of acetic acid and 20 g of a standard commercial hydrogenation catalyst (Raney cobalt) were introduced into a 0.7 litre capacity hydrogenation autoclave, after which the autoclave was heated to approximately 80°C under a hydrogen pressure of approximately 100 atms.
The hydrogen pressure was then increased to 250 atms, and a solution of 100 g of phorone in 100 ml of methanol was pumped in over a period of about 1 hour, during which the hydrogen pressure was kept between 225 and 250 atms.
Hydrogenation was over after about 20 minutes.
The reaction solution was then filtered off from the catalyst and subjected to fractional distillation, yielding 47 g (41.5percent of the theoretical yield) of 4-amino-2,2,6,6-tetramethyl piperidine with a boiling point of 80° to 91°C/16-18 Torr.
38% With acetic acid In methanol EXAMPLE 4
100 ml of methanol, 110 ml (approximately 4 moles) of liquid ammonia, 1 ml of acetic acid and 15 g of standard commercial hydrogenation catalyst (Raney cobalt) were introduced into a 0.7 litre capacity hydrogenation autoclave.
The autoclave was heated to 80°C under a hydrogen pressure of about 80 to 100 atms, after which the hydrogen pressure was kept at around 180 atms.
A solution of 100 g of phorone in 100 ml of methanol was pumped in over a period of about 1 hour.
Hydrogenation was over after about 45 minutes.
After cooling, the autoclave was vented, the reaction solution was filtered off from the catalyst and subjected to fractional distillation, yielding 43 g (38percent of the theoretical yield) of 4-amino-2,2,6,6-tetramethyl piperidine with a boiling point of 82°-92°C/15-16 Torr.

Reference: [1] Patent: US4001250, 1977, A,
[2] Patent: US4001250, 1977, A,
[3] Patent: US4001250, 1977, A,
[4] Patent: US4001250, 1977, A,
[5] Patent: US4001250, 1977, A,
  • 2
  • [ 504-20-1 ]
  • [ 7440-48-4 ]
  • [ 36768-62-4 ]
YieldReaction ConditionsOperation in experiment
65.5% With ammonia; acetic acid In methanol EXAMPLE 7
100 ml of methanol, 150 ml of liquid ammonia, 1 ml of acetic acid and 15 g of Raney cobalt were introduced into a 0.7 litre capacity hydrogenation autoclave.
The autoclave was heated to approximately 180°C under a hydrogen pressure of 80 to 100 atms, after which a solution of 100 g of phorone in 100 ml of methanol was pumped in over a period of 1 hour.
After about 30 minutes, the fall in pressure and, hence, hydrogenation was over.
After cooling, the autoclave was vented and the reaction solution filtered off from the catalyst and subjected to fractional distillation, yielding 74 g (65.5percent of the theoretical yield) of 4-amino-2,2,6,6-tetramethyl piperidine with a boiling point of 90° to 93°C/18 Torr.
Reference: [1] Patent: US4001250, 1977, A,
  • 3
  • [ 504-20-1 ]
  • [ 1197-66-6 ]
YieldReaction ConditionsOperation in experiment
53% With hydrogenchloride In water at 40℃; for 48 h; 5 g of commercial phorone are dissolved in 36 ml of a IM solution of hydrochloric acid and heated at 40°C for 2 days. The reaction mixture is distilled (63-65°C) so as to give 3.0 g of a yellowish oil. Yield = 53percent.1H NMR (DMSO D6, 400 MHz) : 1.25 (m, 4H); 2.3 (m, 12H) .
25% With hydrogenchloride In water at 45℃; for 168 h; Step 1. 2,2,6,64etramethyIdihydro-2H-pyran4(3H)-one: To a stirred solution of 2,6 diniethyihepta-2.5--dien-4one (100 g, 0.724 mol) was added 6N HC1 (600 mL). then the reaction mixture was heated to 45 °C for 7 days, Upon completion, the reaction was quenched with ice cold water and extracted with ethyl acetate (4 x 1 50 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, andconcentrated under reduced pressure to provide a residue. Purification by column chromatography on silica gel (i00200 mesh) using ethyl acetate in hexanc afforded the title compound as a yellow liquid. (yield 28 g, 25percent)
25% at 45℃; for 168 h; Step 1.
2,2,6,6-tetramethyldihydro-2H-pyran-4(3H)-one
To a stirred solution of 2,6-dimethylhepta-2,5-dien-4-one (100 g, 0.724 mol) was added 6N HCl (600 mL), then the reaction mixture was heated to 45° C. for 7 days.
Upon completion, the reaction was quenched with ice cold water and extracted with ethyl acetate (4*150 mL).
The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide a residue.
Purification by column chromatography on silica gel (100-200 mesh) using ethyl acetate in hexane afforded the title compound as a yellow liquid. (yield 28 g, 25percent)
Reference: [1] Patent: WO2010/63773, 2010, A1, . Location in patent: Page/Page column 23-24
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1425 - 1435
[3] Tetrahedron Letters, 1999, vol. 40, # 38, p. 6909 - 6912
[4] Patent: WO2015/23289, 2015, A1, . Location in patent: Page/Page column 52
[5] Patent: US2015/51225, 2015, A1, . Location in patent: Paragraph 0320; 0321
[6] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1943, p. 206[7] Chem.Abstr., 1944, p. 1730
[8] Patent: WO2005/12220, 2005, A2, . Location in patent: Page/Page column 68
[9] Patent: WO2014/41349, 2014, A1, . Location in patent: Page/Page column 31
[10] Patent: US2015/45327, 2015, A1, . Location in patent: Paragraph 0700-0701
[11] Patent: WO2015/18823, 2015, A1, . Location in patent: Paragraph 00207
  • 4
  • [ 3682-91-5 ]
  • [ 1197-66-6 ]
  • [ 504-20-1 ]
Reference: [1] Journal of the Chemical Society, 1944, p. 338
  • 5
  • [ 504-20-1 ]
  • [ 108-82-7 ]
Reference: [1] Chemische Berichte, 1910, vol. 43, p. 3397
[2] Annales de Chimie (Cachan, France), 1914, vol. <9> 1, p. 173[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1912, vol. 155, p. 286
[4] Chemische Berichte, 1909, vol. 42, p. 1635
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 95
  • 6
  • [ 7647-01-0 ]
  • [ 504-20-1 ]
  • [ 563-41-7 ]
Reference: [1] Chemische Berichte, 1903, vol. 36, p. 4382
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