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[ CAS No. 41838-46-4 ]

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Chemical Structure| 41838-46-4
Chemical Structure| 41838-46-4
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CAS No. :41838-46-4 MDL No. :MFCD01570549
Formula : C6H14N2 Boiling Point : 141°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :114.19 g/mol Pubchem ID :2737531
Synonyms :

Safety of [ 41838-46-4 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405 UN#:2920
Hazard Statements:H225-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 41838-46-4 ]

  • Upstream synthesis route of [ 41838-46-4 ]
  • Downstream synthetic route of [ 41838-46-4 ]

[ 41838-46-4 ] Synthesis Path-Upstream   1~23

  • 1
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YieldReaction ConditionsOperation in experiment
100% With ammonium formate In methanol Step: 3A-1Synthesis of l-Methyl-piperidin-4-yIamineProcedure:Ammonium formate (2.226g, 0.035348mol) was added to a solution of 1 -Methyl- piperidin-4-one (lg, 0.008837mol) in MeOH and stirred for lOmins. 20percent Pd-C was added to this and the reaction mixture was heated at 60°C for 2hrs. The reaction was monitored by the TLC (10percent methanol in chloroform). The reaction mixture was filtered through celite bed, concentrated to afford lg (100percent yield) of l-Methyl-piperidin-4-ylamine.
1.4 g With palladium 10% on activated carbon; ammonium formate In methanol; water at 20℃; for 24 h; Ammonium formate (15.4 g; 240 mmol) and 10percent Pd/C (3.14 g; 29 mmol) are added to a solution of 1-methyl-4-piperidone (3.26 mL; 26.5 mmol) in aqueous methanol (80 mL, CH3OH/H2O 9:1); the mixture is stirred for 24 h. at r.t.;. catalyst removal by filtration over Celite and solvent evaporation to dryness at low pressure give a pale yellow residue of 1-methyl-4-aminopiperidine. Dropwise addition of 37percent HCl (4,6 mL) to a stirred solution of said amine in EtOH (50 mL) separates a white precipitate of 1-methyl-4-aminopiperidine hydrochloride that is filteted 18 hrs later, after cooling for 18 hrs at T = + 4°C. Finally, an aqueous solution of the hydrochloride treated with an excess of 0,1 N NaOH (≈ 10 mL) is extracted with CH2Cl2 (3x10 mL). After the usual work-up, solvent evaporation to dryness yields pure 1-methyl-4-aminopiperidine (1.4 g; 12.4 mmol). 1H-NMR (CDCl3): δ 2.85 (m, 2H); 2.58 (m, 1H); 2.25 (s, 3H); 2.01 (m, 2H); 1.85 (m, 2H); 1.63 (bs, 2H, NH2); 1.47 (m, 2H).
Reference: [1] Patent: WO2012/59932, 2012, A1, . Location in patent: Page/Page column 137
[2] Tetrahedron Letters, 2001, vol. 42, # 25, p. 4257 - 4259
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 8, p. 4390 - 4400
[4] Farmaco, 1998, vol. 53, # 3, p. 233 - 240
[5] Yakugaku Zasshi, 1951, vol. 71, p. 1053,1057[6] Chem.Abstr., 1952, p. 5044
[7] Patent: US2006/183769, 2006, A1, . Location in patent: Page/Page column 7
[8] Patent: EP1366018, 2016, B1, . Location in patent: Paragraph 0112
  • 2
  • [ 359878-09-4 ]
  • [ 41838-46-4 ]
YieldReaction ConditionsOperation in experiment
51% With formic acid In methanol for 24 h; Heating / reflux N-((4-methoxyphenyl)methyl)-4-amino-l-methylpiperidine (1 g, 4.27 mmol) was dissolved in 4percent formic acid in methanol (60 mL). 10percent Pd/C (1 g) was added under argon and the reaction mixture was heated to reflux for 24 h. The mixture was filtered through celite and the filtrate was acidified with cone. HCl to pH~l. <n="128"/>Concentration yielded a yellow oil which was purified by flash chromatography (MeOH/CH2Cl2 3:7+3.5percent NH4 OH)to give 249 mg (51percent) of 4-amino-l-methylpiperidine (57-MBT36B) as a white solid. Rf 0.13 (10percent MeOH in CH2Cl2 +3.5percent NH4OH). HPLC- MS (method B) showed MH+ =115. UV/MS(percent)=-/100.
Reference: [1] Patent: WO2007/124136, 2007, A1, . Location in patent: Page/Page column 126-127
  • 3
  • [ 1445-73-4 ]
  • [ 41838-46-4 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride; NaCNBH3 In methanol; diethyl ether a)
4-Amino-1-methylpiperidine
1-Methylpiperidin-4-one (4.22 g, 37 mmol) and an ice cold soln of 1N HCl in Et2 O (37 mL, 37 mmol) were combined.
Trituration followed by evaporation of the Et2 O at 23° under a stream of argon afforded the hydrochloride. MeOH (114 mL), anhydrous NH4 OAc (28.7, 373 mmol) and 3A molecular sieves were added.
Stirred 10 min and then NaCNBH3 (2.33 g; 37 mmol) was added, and the mixture was stirred for 1 h.
Acidified to 2 O.
The resulting mixture was made basic with 50percent aq NaOH and extracted with EtOAc, dried (K2 CO3), and distilled (bp=55°-60°, 15 mm) to afford 3.88 g (88percent) of the title compound.
88% With hydrogenchloride; NaCNBH3 In methanol; diethyl ether a)
4-Amino-1-methylpiperidine
1-Methylpiperidin-4-one (4.22 g, 37 mmol) and an ice cold soln of 1N HCl in Et2 O (37 mL, 37 mmol) were combined.
Trituration followed by evaporation of the Et2 O at 23° under a stream of argon afforded the hydrochloride. MeOH (114 mL), anhydrous NH4 OAc (28.7, 373 mmol) and 3A molecular sieves were added.
Stirred 10 min and then NaCNBH3 (2.33 g, 37 mmol) was added, and the mixture was stirred for 1 h.
Acidified to 2 O.
The resulting mixture was made basic with 50percent aq NaOH and extracted with EtOAc, dried (K2 CO3), and distilled (bp=55°-60°, 15 mm) to afford 3.88 g (88percent) of the title compound.
Reference: [1] Patent: US5593992, 1997, A,
[2] Patent: US5670527, 1997, A,
  • 4
  • [ 359878-55-0 ]
  • [ 41838-46-4 ]
YieldReaction ConditionsOperation in experiment
51% With formic acid; palladium 10% on activated carbon In methanol for 24 h; Inert atmosphere; Reflux Example 88
N-((3-hydroxy-4-methylphenyl)methyl)-N-(1-methylpiperidin-4-yl)-2-(4-methoxyphenyl)acetamide (57MBT54B)
N-((4-methoxyphenyl)methyl)-4-amino-1-methylpiperidine (1 g, 4.27 mmol) was dissolved in 4percent formic acid in methanol (60 mL).
10percent Pd/C (1 g) was added under argon and the reaction mixture was heated to reflux for 24 h.
The mixture was filtered through celite and the filtrate was acidified with conc. HCl to pH 1.
Concentration yielded a yellow oil which was purified by flash chromatography (MeOH/CH2Cl2 3:7+3.5percent NH4OH) to give 249 mg (51percent) of 4-amino-1-methylpiperidine (57-MBT36B) as a white solid. Rf=0.13 (10percent MeOH in CH2Cl2+3.5percent NH4OH). HPLC-MS (method B) showed MH+=115. UV/MS (percent)=-/100.
Reference: [1] Patent: US2015/259291, 2015, A1, . Location in patent: Paragraph 0598
  • 5
  • [ 34737-83-2 ]
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Reference: [1] Patent: EP1227092, 2002, A2, . Location in patent: Page 32
[2] Patent: EP1229035, 2002, A1, . Location in patent: Page 33
[3] Patent: EP1227091, 2002, A2, . Location in patent: Page 33
  • 6
  • [ 65220-86-2 ]
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Reference: [1] Patent: WO2007/124136, 2007, A1,
  • 7
  • [ 359878-15-2 ]
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Reference: [1] Patent: WO2007/124136, 2007, A1,
  • 8
  • [ 359879-83-7 ]
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Reference: [1] Patent: WO2007/124136, 2007, A1,
  • 9
  • [ 359877-52-4 ]
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Reference: [1] Patent: WO2007/124136, 2007, A1,
  • 10
  • [ 41979-39-9 ]
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Reference: [1] Patent: WO2007/124136, 2007, A1,
  • 11
  • [ 79099-07-3 ]
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Reference: [1] Patent: WO2007/124136, 2007, A1,
  • 12
  • [ 118306-22-2 ]
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Reference: [1] Patent: US4410527, 1983, A,
  • 13
  • [ 118306-21-1 ]
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Reference: [1] Patent: US4410527, 1983, A,
  • 14
  • [ 118306-23-3 ]
  • [ 41838-46-4 ]
Reference: [1] Patent: US4410527, 1983, A,
  • 15
  • [ 84540-61-4 ]
  • [ 41838-46-4 ]
Reference: [1] Farmaco, 1998, vol. 53, # 3, p. 233 - 240
  • 16
  • [ 1515-27-1 ]
  • [ 41838-46-4 ]
Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 1053,1057[2] Chem.Abstr., 1952, p. 5044
  • 17
  • [ 145344-76-9 ]
  • [ 41838-46-4 ]
Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 1053,1057[2] Chem.Abstr., 1952, p. 5044
  • 18
  • [ 62718-28-9 ]
  • [ 41838-46-4 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 968[2] Chem.Abstr., 1957, p. 2771
  • 19
  • [ 13221-89-1 ]
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Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 1053,1057[2] Chem.Abstr., 1952, p. 5044
  • 20
  • [ 1515-27-1 ]
  • [ 64-17-5 ]
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Reference: [1] Journal of the Chemical Society, 1957, p. 3165,3171
  • 21
  • [ 41838-46-4 ]
  • [ 755038-02-9 ]
Reference: [1] Patent: US2006/35903, 2006, A1, . Location in patent: Page/Page column 21
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 7, p. 764 - 769
  • 22
  • [ 41838-46-4 ]
  • [ 755039-56-6 ]
  • [ 755038-02-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 40, p. 9378 - 9381
[2] Patent: WO2006/18182, 2006, A1, . Location in patent: Page/Page column 48; 76
[3] Patent: WO2006/18185, 2006, A2, . Location in patent: Page/Page column 48; 76
[4] Patent: US2004/176380, 2004, A1, . Location in patent: Page/Page column 15-16
[5] Patent: WO2004/76454, 2004, A1, . Location in patent: Page/Page column 49; 62
[6] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7785 - 7795
  • 23
  • [ 41838-46-4 ]
  • [ 1137867-66-3 ]
  • [ 1137868-52-0 ]
Reference: [1] Patent: WO2009/42711, 2009, A1, . Location in patent: Page/Page column 359; 388
[2] Patent: US2009/318408, 2009, A1, . Location in patent: Page/Page column 70
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1247 - 1250
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 12, p. 3662 - 3666
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