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[ CAS No. 477600-70-7 ] {[proInfo.proName]}

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Chemical Structure| 477600-70-7
Chemical Structure| 477600-70-7
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Product Details of [ 477600-70-7 ]

CAS No. :477600-70-7 MDL No. :MFCD09475548
Formula : C14H22N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 218.34 Pubchem ID :-
Synonyms :

Safety of [ 477600-70-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 477600-70-7 ]

* 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 [ 477600-70-7 ]
  • Downstream synthetic route of [ 477600-70-7 ]

[ 477600-70-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 32018-96-5 ]
  • [ 6998-30-7 ]
  • [ 477600-70-7 ]
YieldReaction ConditionsOperation in experiment
61% With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-3,5-di-tert-butyl-4-methoxyphenyl-(6,6’-dimethoxybiphenyl-2,2’-diyl)-bis(diphenylphosphine); hydrogen In methanol; dichloromethane at 20℃; for 18 h; Procedure: MeNH3.OAc was formed by slowly adding MeNH2 (33 wtpercent EtOH) to a solution of dry acetic acid in toluene. Upon removal of the volatile components, a white hygroscopic salt was obtained. MeNH3.OAc was used as a reagent to convert ketone 2 into imine 3 in presence of the hydrogenation catalysts, acetic acid, and hydrogen. (1 .4eq/substrate 2) Same catalysts as described above tested with/without l2 in MeOH and in IPA. Hydrogenation conditions: Ir (0.001 mmol), I2 (0 or 0.002mmol), substrate 2 (0.05mmol), IPA or MeOH = 1 ml_, 50 bar H2, R.T., 18h.
Reference: [1] Patent: WO2018/60512, 2018, A1, . Location in patent: Page/Page column 14; 15
  • 2
  • [ 1615709-89-1 ]
  • [ 477600-70-7 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 30℃; for 16 h;
Stage #2: at 30℃;
Add 1-benzyl-3-methylamino-4-methyl-pyridine bromide 15 (10 g, 34.1 mmol) to a 250 ml reaction vial, add ethanol (100 g), and start stirring at a temperature below 30 °C. Add sodium borohydride (3.87 g, to the reaction solution,102.3 mmol), after the addition was completed, the reaction solution was stirred for 16 hours, and the compound 15 was detected by HPLC to be less than 1percent.2M HCl was added dropwise to the reaction solution, no bubbles were formed in the reaction system, and the reaction solution was concentrated to a one-third volume under reduced pressure.It was extracted twice with dichloromethane and the organic phases were combined and concentrated under reduced pressure to basic solvent free.To the crude product, ethanol (40 g) was added, and 2M hydrochloric acid ethanol (20 ml) was added dropwise at a temperature below 30 °C, and a solid precipitated. After the addition, stirring was continued for 1 hour, suction filtration, and the filter cake was dried under reduced pressure.Obtained a white product (6.9 g, 23.8 mmol),The yield was 70percent.
Reference: [1] Patent: CN108610279, 2018, A, . Location in patent: Paragraph 0014; 0016
  • 3
  • [ 923036-27-5 ]
  • [ 477600-70-7 ]
YieldReaction ConditionsOperation in experiment
68 % ee With hydrogen In tetrahydrofuran; ethanol at 70℃; for 48 h; Example 1; Preparation of enriched -(3R, 4R)-(1-benzyl-4-methyl-piperidine-3-yl)-methylamine via Asymmetric Hydrogenation.; Step A. Preparation of1-benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide to a clean, dry, nitrogen purged 500 mL flask were added (4-methyl-pyridin-3-yl)-carbamic acid methyl ester (25.0 g, 150 mmol), toluene (250 ml) and benzyl bromide (28.3 g, 165 mmol). The reaction was heated to 1100C for at least 20 hours. After cooling to between 20-250C the reaction was filtered and the resulting solids washed with toluene (100 ml). After drying under vacuum for at least 12 hours between 40-500C with a slight nitrogen bleed (1-benzyl-4-methyl-pyridin-3-yl)-carbamic acid methyl ester bromide (48.6 g, 144 mmol) was isolated in 96.1percent yield (greater than 95percent purity by NMR).To a suitably sized reaction vessel were added 1-benzy.-3-methoxycarbonylaminσ-4-methyl- pyridinium bromide (150 mg, 0.446 mmoles) , bis(1,5-cyclooctadiene)rhodium (I) trifluoromethanesulfonate (11 mg, 0.0223 mmoles available from Strem Chemical Co. Newburyport, Massachusetts) and (R)-(-)-1 - [(S)-2-(diphenylphosphino)ferrocenyl]ethyIdi-t-butylphosphine(32 mg, 0.033 mmoles - available from Solvias, Basel, Switzerland). The solids were purged with nitrogen (5x at 90 psi) then degassed THF (2 ml) and degassed ethanol (1 ml) were added. The mixture was purged with nitrogen (5x at 90 psi) followed by hydrogen (1x at 210 psi). The reaction mixture was heated to 70 EPO <DP n="20"/>0C then pressurized with hydrogen to 200 psi. After 48 h, the mixture was cooled to 30 0C and purged with nitrogen (5x at 90 psi). An aliquot was removed for GCMS analysis.Sample preparation: 100 μl_ aliquot of reaction mixture is diluted in 1 mL MeOH. Add 10 μL triethylamine. Mix. Filter off precipitates. Analyze on GC MS (column Cyclosil B, temperature gradient 140 - 240 0C, 2 degrees per minute) GC MS analysis: 84percent cis product 68percent ee, 2 percent trans product, 4percent debenzylation byproduct, 3percent alkene intermediate)Alternatively, chiral HPLC may also be used for the analysis. Analysis performed on Agilent1100 system: HPLC conditions: Daicel Chiralcel OJ 4.6 mm x 250 mm analytical column, 5percent Ethanol / hexanes, flow 1 ml/ min, 210 nm, 20 minute run.
Reference: [1] Patent: WO2007/12953, 2007, A2, . Location in patent: Page/Page column 18-19
  • 4
  • [ 923036-28-6 ]
  • [ 477600-70-7 ]
YieldReaction ConditionsOperation in experiment
66 % ee With hydrogen In tetrahydrofuran; ethanol for 48 h; Example 3; Preparation of enriched (3R, 4R)-(1-benzyl-4-methyl-piperidine-3-yl)-methylamine via Asymmetric Hydrogenation of 1-benzyl-4-methyl-1,2,5,6-tetrahydro-pyridin-3-yl)-carbamic acid methyl ester; To the reaction vessel were added 1-benzyl-4-methyl-1 ,2,5,6-tetrahydro-pyridin-3-yl)-carbamic acid methyl ester (150 mg, 0.577 mmoles) , bis(1,5-cyclooctadiene)rhodium (I) trifluoromethanesulfonate (13 mg, 0.0288 mmoles - available from Strem Chemical Co. Newburyport, Massachusetts) and (R)-(-)-1 - [(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine(32 mg, 0.033 mmoles - available from Solvias, Basel Switzerland). The solids were purged with nitrogen (5x at 90 psi) then degassed THF (2 ml) and degassed ethanol (1 ml) were added. The mixture was purged with nitrogen (5x at 90 psi) followed by hydrogen (1x at 210 psi). The reaction mixture was heated to 70 0C then pressurized with hydrogen to 200 psi. After 48 h, the mixture was cooled to 30 0C and purged with nitrogen (5x at 90 psi). An aliquot was removed for GCMS analysis. GC MS analysis: 97percent cis product 66percent ee, 2 percent trans product. Same analysis by GCMS or chiral HPLC as described above.
Reference: [1] Patent: WO2007/12953, 2007, A2, . Location in patent: Page/Page column 19
  • 5
  • [ 1092578-34-1 ]
  • [ 477600-70-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8012 - 8018
  • 6
  • [ 74-89-5 ]
  • [ 477600-70-7 ]
Reference: [1] Tetrahedron Asymmetry, 2017, vol. 28, # 1, p. 105 - 109
  • 7
  • [ 3430-27-1 ]
  • [ 477600-70-7 ]
Reference: [1] Patent: CN108610279, 2018, A,
  • 8
  • [ 100-46-9 ]
  • [ 477600-70-7 ]
Reference: [1] Tetrahedron Asymmetry, 2017, vol. 28, # 1, p. 105 - 109
  • 9
  • [ 477600-70-7 ]
  • [ 479633-63-1 ]
  • [ 923036-30-0 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In water at 100℃; for 16 h; Dissolve the compound (3R,4R)-1-benzyl-N,4-dimethyl-piperidin-3-amine (4.3 g, 19.7 mmol, 1.0 eq.)In 180 ml of water, the compound 4-chloro-7-(p-toluenesulfonyl)-pyrrolo[2,3-d]pyrimidine is then added thereto.(12.3 g, 39.2 mmol, 2.0 eq.) and potassium carbonate (16.6 g, 119 mmol, 6.0 eq.). The reaction is performed at 100oC for 16 hoursWhen it is, it is then cooled to room temperature. After adding three times with ethyl acetate (500ml), it is backwashed with water and brine.After drying over sodium sulfate and spin-drying, the resulting crude compound was isolated by column chromatography (ethyl acetate/petroleum ether = 1:1) to give pale yellowThe target compound (8.6 g, yield = 90percent).
Reference: [1] Patent: CN103896946, 2018, B, . Location in patent: Paragraph 0084; 0085; 0086
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8012 - 8018
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