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[ CAS No. 104-63-2 ] {[proInfo.proName]}

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Chemical Structure| 104-63-2
Chemical Structure| 104-63-2
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Product Details of [ 104-63-2 ]

CAS No. :104-63-2 MDL No. :MFCD00002840
Formula : C9H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :XNIOWJUQPMKCIJ-UHFFFAOYSA-N
M.W : 151.21 Pubchem ID :4348
Synonyms :
N-Benzylethanolamine

Calculated chemistry of [ 104-63-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.99
TPSA : 32.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 0.79
Log Po/w (WLOGP) : 0.62
Log Po/w (MLOGP) : 1.26
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.41
Solubility : 5.82 mg/ml ; 0.0385 mol/l
Class : Very soluble
Log S (Ali) : -1.05
Solubility : 13.5 mg/ml ; 0.0894 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.129 mg/ml ; 0.000851 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 104-63-2 ]

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 [ 104-63-2 ]

* 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 [ 104-63-2 ]
  • Downstream synthetic route of [ 104-63-2 ]

[ 104-63-2 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 104-63-2 ]
  • [ 101-32-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 1521 - 1526
  • 2
  • [ 75-21-8 ]
  • [ 100-46-9 ]
  • [ 101-32-6 ]
  • [ 104-63-2 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 2382
  • 3
  • [ 100-39-0 ]
  • [ 141-43-5 ]
  • [ 38336-04-8 ]
  • [ 38336-06-0 ]
  • [ 104-63-2 ]
Reference: [1] Synthetic Communications, 1995, vol. 25, # 6, p. 907 - 913
[2] Synthetic Communications, 1995, vol. 25, # 6, p. 907 - 913
  • 4
  • [ 100-44-7 ]
  • [ 141-43-5 ]
  • [ 38336-04-8 ]
  • [ 38336-06-0 ]
  • [ 104-63-2 ]
Reference: [1] Synthetic Communications, 1995, vol. 25, # 6, p. 907 - 913
  • 5
  • [ 100-39-0 ]
  • [ 104-63-2 ]
  • [ 101-06-4 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetonitrile at 80℃; for 1.5 h; Treat a mixture of 2-(benzylamino)ethanol (0.95 mL, 6.6 mmol) in ACN (35 mL) with potassium carbonate (1.83 g, 13.2 mmol) followed by benzyl bromide (1.18 mL, 9.89 mmol). Heat the reactions mixture at 80° C. for 1.5 hours. Cool the reaction to room temperature and filter the mixture. Concentrate the filtrate under reduced pressure and purify the residue by silica gel column chromatography eluting with a gradient from 0-30percent EtOAc in hexane to give the title compound 1.7 g (100percent). MS (m/z): 242 (M+1).
Reference: [1] Patent: US2016/176896, 2016, A1, . Location in patent: Paragraph 0119
[2] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10086 - 10097
  • 6
  • [ 100-44-7 ]
  • [ 141-43-5 ]
  • [ 101-06-4 ]
  • [ 104-63-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1943, vol. <5>10, p. 347
  • 7
  • [ 104-63-2 ]
  • [ 40987-24-4 ]
Reference: [1] Synthetic Communications, 1980, vol. 10, # 1, p. 59 - 74
[2] Patent: US2013/274253, 2013, A1,
  • 8
  • [ 104-63-2 ]
  • [ 110859-47-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 5, p. 1406 - 1413
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 5, p. 1406 - 1413
[3] Journal of Medicinal Chemistry, 1990, vol. 33, # 5, p. 1406 - 1413
[4] Patent: US2012/184543, 2012, A1,
[5] Patent: EP2481739, 2012, A1,
[6] Patent: EP2481739, 2012, A1,
[7] Patent: US2012/184543, 2012, A1,
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 17, p. 5721 - 5726
[9] Patent: WO2012/128582, 2012, A2,
[10] Patent: WO2015/92804, 2015, A1,
  • 9
  • [ 104-63-2 ]
  • [ 135072-32-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 6, p. 683 - 689
[2] Tetrahedron Letters, 1991, vol. 32, # 20, p. 2281 - 2284
  • 10
  • [ 24424-99-5 ]
  • [ 104-63-2 ]
  • [ 121496-39-7 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide In dichloromethane; water at 20℃; for 24 h; A solution of di-tert-butyl dicarbonate (0.01 mol) in CH2CL2 (15 ML) was added dropwise to a solution OF 2-BENZYLAMINO-ETHANOL (0. 01 MOL) in 15 ML OF CH2CL2 and 12 ML of 1M NaOH. After stirring 24 h at room temperature, the organic layer was separated, washed with water (25 mL X 2) and dried over anhydrous NA2S04, Removal of solvent under reduced pressure give crude product as an oil, which was purified by column chromatography (silica gel, hexanes: EtOAc, 7: 3) (100percent).
100% With sodium hydroxide In dichloromethane; water at 20℃; for 24 h; Example 25Synthesis of benzyl-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester (III-8) A solution of di-tert-butyl dicarbonate (0.01 mol) in CH2Cl2 (15 mL) was added dropwise to a solution of 2-benzylamino-ethanol (0.01 mol) in 15 mL of CH2Cl2 and 12 mL of 1M NaOH. After stirring 24 h at room temperature, the organic layer was separated, washed with water (25 mL .x. 2) and dried over anhydrous Na2SO4, Removal of solvent under reduced pressure give crude product as an oil, which was purified by column chromatography (silica gel, hexanes:EtOAc, 7:3) (100percent).
100% at 20℃; for 16 h; BOC2O (16.67 g, 76.39 mmol) was added to a solution of 2-(benzylamino)ethanol (11.00 g, 72.75 mmol) in THF (220 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10→60percent ethyl acetate/hexane) to give tert-butyl benzyl(2-hydroxyethyl)carbamate (18.26 g, 72.7 mmol, 100percent) as a colorless oil.
100% at 20℃; for 16 h; Boc2O (16.7 g, 76.4 mmol) was added to a solution of 2-(benzylamino)ethanol (11.0 g, 72.8 mmol) in THF (220 ml) at room temperature.After being stirred at room temperature for 16 h, thereaction mixture was concentrated in vacuo. The residual oil waspurified by column chromatography on silica gel (eluted with10percent–60percent EtOAc in hexane) to give 37 (18.3 g, quant.) as a colorlessoil. 1H NMR (300 MHz, CDCl3) d 0.47 (9H, s), 3.03 (1H, brs), 3.40(2H, brs), 3.65–3.75 (2H, m), 4.48 (2H, brs), 7.21–7.37 (5H, m).LC/MS m/z 152.2 (M+H–(Boc)).
100% With sodium hydroxide In dichloromethane; water at 20℃; for 24 h; Example 25Synthesis of benzyl-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester (III-8) A solution of di-tert-butyl dicarbonate (0.01 mol) in CH2Cl2 (15 mL) was added dropwise to a solution of 2-benzylamino-ethanol (0.01 mol) in 15 mL of CH2Cl2 and 12 mL of 1M NaOH. After stirring 24 h at room temperature, the organic layer was separated, washed with water (25 mL .x. 2) and dried over anhydrous Na2SO4, Removal of solvent under reduced pressure give crude product as an oil, which was purified by column chromatography (silica gel, hexanes:EtOAc, 7:3) (100percent).
92% With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0333333 h; Green chemistry General procedure: Amine (1 mmol) was added to the mixture of (Boc)2O (1 mmol) and DSIMHS (6.5 mg, ~ 0.02 mmol) with constant stirring at room temperature under solvent-free conditions. After completion of the reaction (monitored by TLC),   ethyl acetate (3 × 5 mL) was added to the reaction mixture and the catalyst was decanted and washed with ethyl acetate (2 × 5 mL) and dried. The product was purified by column chromatography, using   ethyl acetate–petroleum ether (2:8) eluent.
78.4% With sodium hydroxide In 1,4-dioxane; water at 5 - 20℃; for 73 h; To a solution of 4.7 ml (5.0 g, 33.1 mmol) of 2-(benzylamino)ethanol in 100 ml of dioxane, cooled to 8-1O0C, a solution of 1.32 g (33.1 mmol) of NaOH in 12 ml of water was slowly <n="59"/>added. The mixture was maintained at 50C and a solution of 7.22 g (33.1 mmol) of di-tert- butyl dicarbonate in 50 ml of dioxane was added drop by drop. The reaction mixture was stirred 1 hour at 50C and at room temperature for 72 hours. After this reaction time, the solvent was removed under reduced pressure. The obtained residue was treated with water and extracted with ethyl acetate several times. The organic extracts were combined, dried (MgSO4), and concentrated to dryness. The resulting product was purified by column chromatography on silica gel performing a gradient elution using hexane/ethyl acetate (90:10 -> 50:50) as eluents. Appropiate fractions were combined and concentrated. The title compound was obtained as an oil. (6.51 g, 78.4percent).
70% With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 18 h; A. A 50 ml_ round bottom was charge with 2-benzylamino-ethanol 8a(284 mg, 1.85 mmol), dioxane (4.0 ml_), and 1 N NaOH (4.0 ml_); and cooled with an ice/water bath. A portion of di-ferf-butyl dicarbonate (500 mg, 2.29 mmo.) was added to the mixture, which was stirred for 18 h at room temperature. The pH was adjusted to 4 with 1 N HCI and extract with DCM (3 X 50 ml_). The organic layer was dried using Na2SO4, filtered through Celite.(R)., and concentrated in vacuo to give 330 mg (70percent) of Compound 8b as a clear glass-like oil. 1H NMR (300 MHz, CDCI3) δ 7.24-7.33 (m, 5 H), 4.48 (bs, 2 H), 3.56-3.74 (bs, 2 H)1 3.29-3.44 (bs, 2 H), 1.42 (s, 9 H).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 3, p. 295 - 300
[2] Journal of Organic Chemistry, 2000, vol. 65, # 20, p. 6368 - 6380
[3] Patent: WO2005/26111, 2005, A2, . Location in patent: Page/Page column 17
[4] Patent: WO2008/42353, 2008, A1, . Location in patent: Page/Page column 19; 21
[5] Patent: TW2016/2105, 2016, A, . Location in patent: Paragraph 0563
[6] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 2, p. 470 - 482
[7] Patent: WO2008/42353, 2008, A1, . Location in patent: Page/Page column 19; 21
[8] Journal of Medicinal Chemistry, 1999, vol. 42, # 11, p. 2007 - 2020
[9] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5865 - 5868
[10] Synthesis, 2001, # 4, p. 550 - 552
[11] Monatshefte fur Chemie, 2012, vol. 143, # 4, p. 631 - 635
[12] Comptes Rendus Chimie, 2014, vol. 17, # 2, p. 164 - 170
[13] Tetrahedron Letters, 2008, vol. 49, # 21, p. 3527 - 3529
[14] Synthesis, 2008, # 19, p. 3126 - 3130
[15] Comptes Rendus Chimie, 2010, vol. 13, # 5, p. 544 - 547
[16] Catalysis Communications, 2011, vol. 12, # 12, p. 1088 - 1094
[17] Letters in Organic Chemistry, 2011, vol. 8, # 1, p. 38 - 42
[18] Journal of the Iranian Chemical Society, 2012, vol. 9, # 4, p. 495 - 502
[19] Journal of Molecular Liquids, 2013, vol. 177, p. 386 - 393
[20] RSC Advances, 2015, vol. 5, # 26, p. 19790 - 19798
[21] Synthetic Communications, 1993, vol. 23, # 17, p. 2443 - 2449
[22] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 7, p. 1137 - 1147
[23] Patent: WO2007/124898, 2007, A1, . Location in patent: Page/Page column 57-58
[24] Patent: WO2007/81995, 2007, A2, . Location in patent: Page/Page column 189
[25] Tetrahedron, 1998, vol. 54, # 23, p. 6385 - 6402
[26] Patent: WO2005/123747, 2005, A1, . Location in patent: Page/Page column 83
  • 11
  • [ 34619-03-9 ]
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  • [ 121496-39-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 3, p. 779 - 797
  • 12
  • [ 104-63-2 ]
  • [ 121496-39-7 ]
Reference: [1] Patent: US6214833, 2001, B1,
  • 13
  • [ 104-63-2 ]
  • [ 305857-34-5 ]
  • [ 121496-39-7 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 20, p. 6368 - 6380
  • 14
  • [ 298-12-4 ]
  • [ 104-63-2 ]
  • [ 287930-73-8 ]
YieldReaction ConditionsOperation in experiment
91% Reflux To a 250ml reaction flask was added 50percent glyoxylic acid (67ml, 0.61mol) and tetrahydrofuran (130ml), heated to reflux, was added dropwise N- benzyl ethanolamine (41.5g, 0.27mol) in tetrahydrofuran (20ml) solution, to the reaction complete, the tetrahydrofuran was evaporated, water (170ml), cooled with stirring, to precipitate a solid, ice-water bath was stirred for 30 minutes, filtered and washed with ice water, drying in a yellowish solid, i.e. compounds of formula VII (51.8g, 91percent), mp132 ~ 136 .
Reference: [1] Patent: CN103030668, 2016, B, . Location in patent: Paragraph 0031-0033
[2] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2129 - 2135
  • 15
  • [ 104-63-2 ]
  • [ 287930-73-8 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 48, p. 8917 - 8920
[2] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2129 - 2135
  • 16
  • [ 104-63-2 ]
  • [ 563-96-2 ]
  • [ 287930-73-8 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 48, p. 8917 - 8920
  • 17
  • [ 109745-70-2 ]
  • [ 104-63-2 ]
  • [ 287930-73-8 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 8, p. 2129 - 2135
  • 18
  • [ 108228-02-0 ]
  • [ 104-63-2 ]
  • [ 287930-73-8 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 48, p. 8917 - 8920
  • 19
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  • [ 287930-73-8 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 48, p. 8917 - 8920
  • 20
  • [ 104-63-2 ]
  • [ 135072-15-0 ]
Reference: [1] Patent: WO2012/128582, 2012, A2,
  • 21
  • [ 104-63-2 ]
  • [ 769087-80-1 ]
Reference: [1] Patent: WO2015/164508, 2015, A1,
  • 22
  • [ 104-63-2 ]
  • [ 84761-04-6 ]
Reference: [1] Patent: US2016/289171, 2016, A1,
  • 23
  • [ 104-63-2 ]
  • [ 165894-09-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5684 - 5688
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