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Chemistry
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benzylamino
4-(Benzylamino)butan-1-ol
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benzylamino

[ CAS No. 59578-63-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 59578-63-1
Chemical Structure| 59578-63-1
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Product Details of [ 59578-63-1 ]

CAS No. :59578-63-1 MDL No. :MFCD00191609
Formula : C11H17NO Boiling Point : -
Linear Structure Formula :- InChI Key :SNRCGOVPZJPRQZ-UHFFFAOYSA-N
M.W : 179.26 Pubchem ID :1790018
Synonyms :

Safety of [ 59578-63-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 59578-63-1 ]

* 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.

  • Downstream synthetic route of [ 59578-63-1 ]

[ 59578-63-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 59578-63-1 ]
  • [ 29897-82-3 ]
Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 312 - 315
[2]Organic Letters,2013,vol. 15,p. 5178 - 5181
[3]Journal of the Chemical Society. Chemical communications,1981,p. 611 - 612
[4]Organic Syntheses,2013,vol. 90,p. 251 - 260
  • 2
  • [ 50-00-0 ]
  • [ 59578-63-1 ]
  • [ 5655-01-6 ]
  • 7-[benzyl(4-hydroxybutyl)amino]methyl}-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% In water at 85℃; 7.1 A mixture of 3-(benzylamine)butanol (172 mg, 0.96 mmol), 9-deazahypoxanthine (100 mg, 0.74 mmol) and 37% aq formaldehyde (72 μl, 0.96 mmol) in water (5 ml) was stirred and heated in stoppered flask at 85°C overnight. The solution was evaporated to dryness and the residue was chromatographed on silica (DCM-MeOH 9:1 to 8:2) to give 7-((benzyl(4- hydroxybutyl)amino)methyl)-3H-pyrrolo[3,2-cdpyrimidin-4(5H)-one (130 mg, 0.40 mmol, 55% yield) as a white solid. 1H NMR (300MHz, CD3OD+DCI) 1.50 (2H, m), 1.93 (2H, m), 3.20 (2H1 q, J 7Hz), 3.55 (2H1 t, J 6Hz), 4.50 (1H, d, J 13Hz), 4.62 (1H, d, J 13Hz), 4.72 (1H, d, J 14.1Hz), 4.79 (1H, d, J 14.1Hz), 7.45 (3H, m), 7.63 (2H, m), 8.00 (1H, s), 9.10 (1H, s); 13C NMR (75MHz, CD3OD+DCI) 22.2, 30.8, 50.0, 53.6, 58.2, 62.3, 100.2, 103.7, 120.4, 130.7, 131.4, 132.7, 133.5, 134.5, 147.1, 153.0.
55% In water at 85℃; for 16h;
Reference： [1]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - WO2008/30119, 2008, A1 Location in patent: Page/Page column 35
[2]Location in patent: experimental part Clinch, Keith; Evans, Gary B.; Frohlich, Richard F. G.; Furneaux, Richard H.; Kelly, Peter M.; Legentil, Laurent; Murkin, Andrew S.; Li, Lei; Schramm, Vern L.; Tyler, Peter C.; Woolhouse, Anthony D. [Journal of Medicinal Chemistry, 2009, vol. 52, # 4, p. 1126 - 1143]
  • 3
  • [ 41270-66-0 ]
  • [ 59578-63-1 ]
  • 4-[(benzyl)(5,6-diphenylpyrazin-2-yl)amino]-1-butanol [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6692 - 6704
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 7128 - 7137
  • 4
  • [ 1000885-94-8 ]
  • [ 59578-63-1 ]
  • [ 98648-05-6 ]
  • [ 1000886-00-9 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: 4-(benzylamino)-1-butanol; 6-oxo-hexyl-carbamic acid benzyl ester In toluene at 20℃; for 0.25h; Stage #2: methyl 2-(1-isocyanocyclohexanecarboxamido)acetate With ammonium chloride In toluene at 60℃; Further stages.;
Reference： [1]Pirali, Tracey; Tron, Gian Cesare; Masson, Geraldine; Zhu, Jieping [Organic Letters, 2007, vol. 9, # 25, p. 5275 - 5278]
  • 5
  • [ 1214385-51-9 ]
  • [ 59578-63-1 ]
  • N-(4-((3H-[1,2,3]triazole[4,5-b]pyridine-3-yl)oxy)butyl)-N-benzyl-5-bromo-6-hydroxypicolinamide [ No CAS ]
Reference： [1]Organic Letters,2013,vol. 15,p. 642 - 645
  • 6
  • [ 2508-29-4 ]
  • [ 100-52-7 ]
  • [ 59578-63-1 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 5-hydroxypentylamine; benzaldehyde In methanol at 20℃; for 0.166667h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; 3.7.1 General procedure for the synthesis of Bn-protected amino alcohols 12a,b General procedure: The amino alcohol 21 (1.0 equiv) was dissolved in MeOH ([21] = 0.5 mol/L), then benzaldehyde [24] (1.3 equiv) was added and the mixture was allowed to stir for 10 min at room temperature. Subsequently, the reaction was cooled in an ice bath, NaBH4 (1.3 equiv) was added portionwise, the mixture was stirred for 0.25 h at 0 °C and 2 h at ambient temperature. Next, the reaction suspension was cooled again to 0 °C, conc. HCl-solution in water (3.0 equiv) was added dropwise and MeOH was removed under reduced pressure ( 100 mbar). The residue was diluted with water (1 mL/1 mmol 21) and Et2O (H2O/Et2O 2:1; pH of the mixture ≤ 0), the phases were separated and the aqueous phase was washed with further Et2O (2x, H2O/Et2O 2:1). In the following,the aqueous phase was cooled in an ice bath, KOH (2.5 equiv) was added and dissolved under stirring, whereby an oil separated. The basic mixture was extracted with Et2O (3x, H2O/Et2O 2:1), the combined extraction phases were dried over MgSO4 and concentrated under reduced pressure. The crude benzylamine 12 was dissolved in 1 mL of chloroform and concentrated under reduced pressure (2x) to remove residual Et2O and dried in high vacuum for 0.5 h under stirring (until the gas evolution ceased).
Reference： [1]Huy, Peter H.; Westphal, Julia C.; Koskinen, Ari M.P. [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 369 - 383]
  • 7
  • [ 59578-63-1 ]
  • [ 2905-56-8 ]
YieldReaction ConditionsOperation in experiment
63% With iodine; triethylamine; triethyl phosphite; In dichloromethane; at -78 - 20℃;Inert atmosphere; General procedure: Under an atmosphere of argon the amino alcohol/diol (rac-)12 (1.0 equiv, 1-2 mmol) was dissolved in NEt3 (6.0 equiv) and dry CH2Cl2 (NEt3/CH2Cl2 1:2), the mixture was cooled to -78 C in an acetone/dryice bath and treated with P(OEt)3 (1.4 equiv). Subsequently, iodine (1.2 equiv) was added in oneportion and the mixture was stirred at -78 C until complete dissolution of iodine (2.5-5 h). Then the cooling bath was removed and the clear reaction solution was allowed to stir at ambient temperature for 0.5 h [25].
Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 369 - 383

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