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Chemical Structure| 622-26-4
Chemical Structure| 622-26-4
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Product Details of [ 622-26-4 ]

CAS No. :622-26-4 MDL No. :MFCD00006008
Formula : C7H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :LDSQQXKSEFZAPE-UHFFFAOYSA-N
M.W : 129.20 Pubchem ID :73953
Synonyms :

Calculated chemistry of [ 622-26-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.53
TPSA : 32.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : 0.21
Log Po/w (WLOGP) : -0.01
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 1.23
Consensus Log Po/w : 0.75

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.64
Solubility : 29.5 mg/ml ; 0.228 mol/l
Class : Very soluble
Log S (Ali) : -0.45
Solubility : 46.2 mg/ml ; 0.358 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.28
Solubility : 6.7 mg/ml ; 0.0519 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 622-26-4 ]

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 [ 622-26-4 ]

* 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 [ 622-26-4 ]
  • Downstream synthetic route of [ 622-26-4 ]

[ 622-26-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 51052-78-9 ]
  • [ 622-26-4 ]
YieldReaction ConditionsOperation in experiment
62.5% With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; Cooling with ice; Inert atmosphere (0.06 mol) of lithium tetrahydride was added to anhydrous tetrahydrofuran (80 mL) under a nitrogen atmosphere under ice-cooling, and 4.95 g (0.03 mol) of pulverized 4-piperidine acetic acid was slowly added to the reaction solution , In which the reaction temperature was controlled to be less than 30 ° C. The reaction was allowed to proceed at 25 ° C overnight. The temperature was lowered to 0 ° C, and 3 mL of water, 3 mL of 30percent aqueous sodium hydroxide and 3 mL of water were gradually added dropwise. The mixture was stirred at 25 ° C for 30 min. The solvent was evaporated under reduced pressure to give 2.23 g (62.5percent) of a light yellow solid.
Reference: [1] Patent: CN103755686, 2016, B, . Location in patent: Paragraph 0099; 0100
  • 2
  • [ 383865-57-4 ]
  • [ 622-26-4 ]
Reference: [1] Patent: US2002/45615, 2002, A1,
  • 3
  • [ 5344-27-4 ]
  • [ 622-26-4 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 2894
[2] Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 1173,1177
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 630,631
  • 4
  • [ 28356-58-3 ]
  • [ 622-26-4 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 13, p. 2343 - 2346
  • 5
  • [ 622-26-4 ]
  • [ 169457-73-2 ]
Reference: [1] Patent: US2011/294754, 2011, A1,
  • 6
  • [ 622-26-4 ]
  • [ 24424-99-5 ]
  • [ 89151-44-0 ]
YieldReaction ConditionsOperation in experiment
98% at 20℃; for 16 h; To a stirred solution of 2-piperidin-4-ylethanol (25.5 g, 197 mmol) in tetrahydrofuran (250 mL) was added di-tert-butyl dicarbonate (43.0 g, 197 mmol) at room temperature.
After 16 h the reaction mixture was concentrated under reduced pressure to provide tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (44.3 g, 98percent) as colorless oil.
1H NMR (300 MHz, CDCl3) δ 4.11-4.05 (m, 2H), 3.72-3.66 (m, 2H), 2.73-2.65 (m, 2H), 1.74-1.59 (m, 4H), 1.55-1.43 (m, 2H), 1.38 (s, 9H), 1.19-1.09 (m, 2H).
95% With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 24 h; 3.25 1-tert-Butyloxycarbonyl-4-hydroxyethyl-piperidine (61KS82)
4-Piperidineethanol (1.05 g, 8.13 mmol) was dissolved in dioxane/water (1:1, 50 mL) followed by the addition of Boc2O (2.13 g, 9.76 mmol) and NaHCO3 (8.62 g, 81.3 mmol).
The mixture was stirred at room temperature for 24 h before extraction with DCM was performed.
The combined organic phase was washed consecutively with citric acid (5percent sol.) and aqueous NaHCO3 followed by drying (Na2SO4), filtration and evaporation of the solvent to give the title compound (61KS82) (1.77 g, 95percent).
1H NMR (CDCl3) δ 1.12 (dq, 2H, J=4.6 Hz, 11.8 Hz), 1.35-1.55 (m, 14H), 2.70 (t, 2H, J=12.8 Hz), 3.70 (t, 2H, J=6.3 Hz, -CH2C2OH), 3.95-4.20 (m, 2H); 13C NMR (CDCl3) δ 28.7 (Boc-H3), 32.8, 39.5, 44.2, 60.5, 67.3, 79.4 (-(CH3)3), 155.1 (C=O).
95% at 0 - 25℃; for 4.25 h; Inert atmosphere To a solution of 2-(piperidin-4-yl)ethanol (2.42 g, 18.7 mmol) in dichloromethane (24 mL) was added under nitrogen at 0 °C di-tert-butyl dicarbonate (4.09 g, 4.35 mL, 18.7 mmol). There was a strong gas evolution The solution was stirred at 0 °C for 15 min and at room temperature for 4 h. The reaction mixture was washed with water (50 mL), potassium hydrogen sulfate (10percent aqueous solution, 50 mL) and brine (50 mL). The aqueous layers were back-extracted with dichloromethane (50 mL). The combined organic layers were dried over sodium sulfate to yield colorless oil (4.1 g, 95 percent). MS: m/z = 230.5 (M+H)+
95% at 20℃; for 2 h; 2-(N-tert-Butoxycarbonyl-4-piperidinyl)ethanol 2-(4-Piperidinyl)ethanol (1.0 g, 7.7 mmol) was dissolved in methanol (50 ml). To this solution, di-tert-butyl carbonate (2.0 g, 9.3 mmol) was added, and the mixture was stirred at room temperature for 2 hours. After the reaction was confirmed by TLC to be complete, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:acetone=9:1) to obtain N-tert-butoxycarbonyl-2-(4-piperidinyl)ethanol (1.68 g, yield: 95percent).
91.83% at 15 - 20℃; for 20 h; 2-(Piperidin-4-yl)ethan-1-ol (3.00 g, 23.22 mmol) was dissolved in 30 mL dichloromethane. Di-tert-butyl dicarbonate (5.22 g, 23.92 mmol) was slowly added portionwise at 15 to 20° C. After that, the reaction mixture was stirred for 20 h at room temperature. The reaction mixture was slowly poured into 50 mL water after the reaction was complete as monitored by TLC. Then, the mixture was extracted with dichloromethane (50 mL×2). The combined organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under vacuum to give a residue. The residue was purified by column chromatography (Height: 250 mm, Diameter, 20 mm, 100-200 slica gel, petroleum/ethyl acetate=3:1, 1:1) to afford 2-(1-tert-butoxycarbonyl-4-piperidyl)ethanol (4.89 g, 91.83percent yield) as a colorless liquid.
91% at 0 - 20℃; To an ice-cold solution of 4-(2-hydroxyethyI) piperidine (4.25 g, 33 mmol) in CH2CI2 (5 ml_) was added a solution of di-te/t-butyl dicarbonate (7.2 g, 33 mmol) in CH2CI2 (30 ml.) over 1 h. The mixture was stirred at r.t. overnight. The solvent was removed. The residue was dissolved in Et2O (5OmL), washed with 1 M aq. NaH2PO4, sat. aq. NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 6.9 g (91percent) of the title compound.13C NMR (CDCI3) δ 154.9, 79.3, 60.1, 44.0, 39.3, 32.5, 32.1, 28.5
88% at 20℃; To A solution of 2- (4-PIPERIDYL) ETHANOL (9. 63 G, 74. 5 MMOL) IN DMF (100 ML) AT 0 C, DI-TERT-BUTYL DICARBONATE (16. 26 g, 5 mol) was added slowly. The mixture was stirred overnight at room temperature. The solvent was concentrated and the residue was dissolved in A mixture of ETOAC and water. The phases were separated. The organic phase was dried over NA2S04 and concentrated to dryness, to afford 15.09 g of the desired product : 88percent).
88% With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 3 h; To a stirred solution of 2-(piperidin-4-yl)ethanol (LXX, lg, 7.72 mmol) in tetrahydrofuran and water mixture (40 mL, 1 : 1) was added sodium bicarbonate (1.62 g, 19.32 mmol) and Boc anhydride (2.6 mL, 11.6 mmol) at room temperature and stirred for 3 h. The reaction mixture was diluted with ethyl acetate and the organic portion was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure to get the crude product which was purified by flash column chromatography using ethylacetate-hexane gradient to afford the titled product as gummy solid (LXXI, 1.6 g, 88 percent). LC-MS m/z calcd for C12H23NO3, 229.2; found 130.2 [M-Boc]+.
87% at 20℃; A mixture of 4-piperidin ethanol (2. 0 g, 15 mmol, 1.0 eq. ) and t-butyl dicarbonate (3. 87 ML, 18.5 MMOL,). 2 eq. ) in anhydrous THF (80 mL) is kept under stirring at room temperature for one night. The solvent is then removed by evaporation under reduced pressure and the raw product obtained purified by flash chromatography using AcOEt : petroleum ether 60 : 40 as eluent mixture. 4-(2-Hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (37) is obtained as a colourless oil (3.1 G, 13.4 mmol, yield = 87percent) HPLC (method A) : Rt = 7.92 min. H1 NMR (No., CDCL3-D3, 300 MHz) : 1.14 (DQ, 2H, Hf, J=6. 3,13. 5 Hz); 1.47 (S, 9H, C (CH3) 3) : 1. 55 (pt, 2H, Hc, J= 6.3 HZ) ; 1. 50-1.65 (m, 1H, Hc); 1.69 (d, 2H, Hd, J=13. 2 Hz); 1.89 (s, 1H, OH) ; 2.71 (LAD, 2H, Hb, J= 2. 1, 12.9 Hz) ; 3.73 (t, 2H, Hg, J= 6.3 Hz) ; 4.10 (m, 2H, Ha).
85.2% With triethylamine In dichloromethane at 0 - 25℃; (0.01 mol) of 4-piperidineethanol, 2.4 ml (0.02 mol) of triethylamine and 30 ml of dichloromethane were charged into a 150 ml three-necked flask. After cooling to 0 ° C, 2.54 g (0.01 mol) of di-t-butyl dicarbonate was slowly added dropwise. After completion of the reaction, the reaction was carried out at 25 ° C overnight. The reaction was terminated by the disappearance of the starting material by TLC (PE: EA = 2: 1). Dichloromethane was distilled off under reduced pressure, 40 ml of ethyl acetate was added thereto, and the mixture was washed with saturated brine, neutralized and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 2.27 g (85.2percent) of a clear oil.
52 g at 20℃; [00482] To a stuffed solution of 2-(piperidin-4-yl)ethanol (30 g, 0.2322 mmol) in i,2-dichloromethane (200 ml) was added in portions di-tert-butyl dicarbonate (53 g, 0.24 mmol) . The resultant mixture was stuffed at room temperature overnight. After confirming reaction completion by thin-layer chromatography, the reaction mixture was washed with water and concentrated to yield compound INT-1(52g).
52 g at 20℃; To a stirred solution of 2-(piperidin-4-yl)ethanol (30 g, 0.2322 mmol) in 1,2-dichloromethane (200 ml) was added in portions di-tert-butyl dicarbonate (53 g, 0.24 mmol) . The resultant mixture was stirred at room temperature overnight. After confirming reaction completion by thin-layer chromatography, the reaction mixture was washed with water and concentrated to yield compound INT-1 (52g).
52 g at 20℃; Preparation of tert-butyl 4-(2-hydroxyethyl)piperidine- 1 -carboxylate (TNT-1):[00491] To a stirred solution of 2-(piperidin-4-yl)ethanol (30 g, 0.2322 mmol) in i,2-dichloromethane (200 ml) was added in portions di-tert-butyl dicarbonate (53 g, 0.24 mmol) . The resultant mixture was stirred at room temperature overnight. After confirming reaction completion by thin-layer chromatography, the reaction mixture was washed with water and concentrated to yield compound INT-1 (52g).

Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 15, p. 2515 - 2516
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2100 - 2107
[4] Patent: EP2202223, 2010, A1, . Location in patent: Page/Page column 52
[5] Journal of the American Chemical Society, 2016, vol. 138, # 16, p. 5433 - 5440
[6] Organic Letters, 2016, vol. 18, # 14, p. 3350 - 3353
[7] Patent: US2004/67931, 2004, A1, . Location in patent: Page/Page column 15
[8] Patent: WO2014/187762, 2014, A1, . Location in patent: Page/Page column 57
[9] Patent: US2015/353489, 2015, A1, . Location in patent: Paragraph 0097; 0137; 0138
[10] Organic and Biomolecular Chemistry, 2014, vol. 12, # 5, p. 783 - 794
[11] Patent: US2018/148452, 2018, A1, . Location in patent: Paragraph 0181-0182
[12] Patent: WO2006/105796, 2006, A1, . Location in patent: Page/Page column 47
[13] Patent: WO2004/76450, 2004, A1, . Location in patent: Page 52
[14] Patent: WO2017/195216, 2017, A1, . Location in patent: Page/Page column 193-194
[15] Patent: WO2004/94412, 2004, A1, . Location in patent: Page 23
[16] Patent: CN103755686, 2016, B, . Location in patent: Paragraph 0101; 0102
[17] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 4, p. 693 - 705
[18] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S785-S786
[19] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 1, p. 119 - 123
[20] Patent: US6664265, 2003, B2, . Location in patent: Page column 33, 34
[21] Patent: WO2004/54973, 2004, A2, . Location in patent: Page 28
[22] Patent: US6303609, 2001, B1,
[23] Patent: US5594023, 1997, A,
[24] Patent: WO2006/46031, 2006, A1, . Location in patent: Page/Page column 78
[25] Patent: US4489075, 1984, A,
[26] Patent: US6248755, 2001, B1,
[27] Patent: WO2006/107771, 2006, A2, . Location in patent: Page/Page column 55-56
[28] Patent: US2003/139441, 2003, A1,
[29] Patent: US6677347, 2004, B2,
[30] Patent: US2007/275906, 2007, A1, . Location in patent: Page/Page column 24-25
[31] Patent: US2008/176901, 2008, A1, . Location in patent: Page/Page column 8
[32] Patent: US6660735, 2003, B2, . Location in patent: Page column 39, 40
[33] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4670 - 4674
[34] Patent: WO2008/97673, 2008, A1, . Location in patent: Page/Page column 24
[35] Patent: WO2008/97676, 2008, A1, . Location in patent: Page/Page column 26
[36] Patent: US2005/107434, 2005, A1, . Location in patent: Page/Page column 13
[37] Patent: EP1602645, 2005, A1, . Location in patent: Page/Page column 15-16
[38] Patent: EP1386920, 2004, A1, . Location in patent: Page 44-45
[39] Patent: WO2004/20435, 2004, A1, . Location in patent: Page 112
[40] Patent: US2011/294754, 2011, A1, . Location in patent: Page/Page column 5
[41] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7480 - 7501
[42] Patent: WO2013/158644, 2013, A2, . Location in patent: Paragraph 00479; 00481; 00482
[43] Patent: US2015/31674, 2015, A1, . Location in patent: Paragraph 0277
[44] Patent: WO2015/38649, 2015, A1, . Location in patent: Paragraph 00532
[45] Patent: US2015/232444, 2015, A1, . Location in patent: Paragraph 0420; 0421
[46] Patent: WO2015/134464, 2015, A2, . Location in patent: Paragraph 00488; 00490
[47] Patent: WO2015/188085, 2015, A1, . Location in patent: Paragraph 0372
[48] Patent: WO2007/122410, 2007, A1, . Location in patent: Page/Page column 80-81
  • 7
  • [ 622-26-4 ]
  • [ 34619-03-9 ]
  • [ 89151-44-0 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; A solution (20 ml) of di-tert-butyl carbonate (8.95 g, 41.0 mmol) in tetrahydrofuran was added dropwise to a solution (80 ml) of 4-piperidineethanol (5.30 g, 41.0 mmol) in tetrahydrofuran at room temperature and stirred overnight.
After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate.
The resulting solution was washed successively with a 1M aqueous hydrochloric acid solution, a saturated aqueous sodium chloride solution, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate.
The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol = 98/2) to obtain the title compound (9.67 g, quantitative).; 1H-NMR(CDCl3) 4.18 (br,2H), 3.66-3.74 (m,2H), 2.69 (br,2H), 1.68 (br,2H), 1.45-1.57 (m,2H).
52 g at 20℃; To a stirred solution of 2-(piperidin-4-yl)ethanol (30 g, 0.2322 mmol) in1 ,2-dichloromethane (200 ml) was added in portions di-tert-butyl dicarbonate (53 g,0.24 mmol) . The resultant mixture was stirred at room temperature overnight. Afterconfirming reaction completion by thin-layer chromatography, the reaction mixturewas washed with water and concentrated to yield compound INT-l (52g).
Reference: [1] Patent: EP1640369, 2006, A1, . Location in patent: Page/Page column 31
[2] Patent: WO2015/143004, 2015, A1, . Location in patent: Paragraph 00829; 00831; 00832
  • 8
  • [ 622-26-4 ]
  • [ 89151-44-0 ]
Reference: [1] Patent: US6194435, 2001, B1,
  • 9
  • [ 123-91-1 ]
  • [ 622-26-4 ]
  • [ 89151-44-0 ]
Reference: [1] Patent: US5861414, 1999, A,
  • 10
  • [ 622-26-4 ]
  • [ 64-19-7 ]
  • [ 89151-44-0 ]
Reference: [1] Patent: US5281585, 1994, A,
  • 11
  • [ 622-26-4 ]
  • [ 146093-46-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
  • 12
  • [ 622-26-4 ]
  • [ 501-53-1 ]
  • [ 122860-33-7 ]
YieldReaction ConditionsOperation in experiment
94.3% With sodium hydroxide In tetrahydrofuran Preparation 29
A mixture of 4-piperidinethanol (2.9 g, 100 mol), THF (350 mL) and 4N NaOH (200 mL) was cooled to 0° C. and a solution of carbobenzyloxy chloride (26.0 mL, 180 mmol) in THF (50 mL) was added at such a rate as to keep the internal reaction temperature below 5° C.
The reaction mixture was stirred at 0° C. for 2 hours, and then partitioned between water (250 mL) and ether (250 mL).
The layers were separated, and the aqueous layer was extracted with ether (2*100 mL).
The ether extracts were combined, washed with brine, dried over MgSO4, filtered through florisil and concentrated in vacuo.
The residue was purified by High Pressure Liquid Chromatography (HPLC) eluding with ethyl acetate to afford 24.8 g (94.3percent) of 4-(2-hydroxymethyl)-1-carbobenzyloxypiperidine.
Reference: [1] Patent: US5512589, 1996, A,
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