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Product Details of [ 122860-33-7 ]

CAS No. :122860-33-7 MDL No. :MFCD02094490
Formula : C14H19NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :LINIORCIRVAZSM-UHFFFAOYSA-N
M.W : 249.31 Pubchem ID :736490
Synonyms :

Calculated chemistry of [ 122860-33-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.59
TPSA : 49.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.84
Log Po/w (XLOGP3) : 1.68
Log Po/w (WLOGP) : 1.49
Log Po/w (MLOGP) : 1.68
Log Po/w (SILICOS-IT) : 1.74
Consensus Log Po/w : 1.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 1.09 mg/ml ; 0.00436 mol/l
Class : Soluble
Log S (Ali) : -2.34
Solubility : 1.14 mg/ml ; 0.00457 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.82
Solubility : 0.377 mg/ml ; 0.00151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.63

Safety of [ 122860-33-7 ]

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 [ 122860-33-7 ]

* 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 [ 122860-33-7 ]
  • Downstream synthetic route of [ 122860-33-7 ]

[ 122860-33-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 122860-33-7 ]
  • [ 138163-08-3 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78 - -55℃; for 0.5 h;
Stage #2: With triethylamine In dichloromethane at -78 - 20℃;
Example 3; 4-Formyl-piperidine-1-carboxylic acid benzyl ester (3); Oxalyl chloride (59.1 ml_, 674 mmol) was dissolved in dichloromethane (500 ml_) and cooled to -78°C. Dimethylsulfoxide (68.3 ml_, 963 mmol) was added and the mixture was stirred for 15 min. 4-Hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (2) (120 g, 481 mmol) dissolved in dichloromethane (500 ml_) was added. The mixture was allowed to warm to -55°C for 15 min. The mixture was again cooled to -78°C and triethylamine (205 ml_, 1443 mmol) in dichloromethane (250 ml_) was added. The suspension was allowed to warm to room temperature and quenched with glacial acetic acid (100 ml_). The solution was washed with water and the aqueous phase extracted with dichloromethane (2 x 200 ml_). The combined organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated to give 4- formyl-piperidine-1-carboxylic acid benzyl ester (119 g, 100percent).
93%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h;
Stage #2: at -78℃; for 0.5 h;
To oxalyl chloride (10.3 mL, 0.120 mol) in 150 mL of DCM and at -78 °C, a solution of DMSO (17.1 mL, 0.241 mol) in DCM (25 mL) was added dropwisely. After 30 min, benzyl 4- (hydroxymethyl)-piperidine-l-carboxylate (20 g, 0.080 mol) in DCM (25 mL) was added dropwisely. After 30 min, Et3N (44.7 mL, 0.321 mol) was added. The resulting solution was stirred for 30 min at -78 °C. The reaction was diluted with water, extracted with DCM (3 x). Combined organic layers were washed with water (3 x 500 mL), dried over Na2S04, filtered and concentrated to give Intermediate 6C (18.5 g, 93.0percent). MS (ESI) m/z 247 (M+H)+.
75% With pyridinium chlorochromate In dichloromethane at 20℃; for 3 h; Example 25;. N-Benzyloxycarbonyl-4- (formyl)-piperidine (E-13).; A stirred suspension of N-(benzyloxycarbonyl)-4-hydroxymethyl)-piperidine (E-12,2 g, 8 mmol) and CeliteTM (4 g) in dry DCM (120 mL) at room temperature was treated with pyridinium chlorochromate (3.5 g, 16.0 mmol), stirred for 3 hours, and filtered on Celte. The filtrate was evaporated to a dark residue which was purified by column chromatography using a gradient of 25 to 50 percent EtOAc in hexane as eluant to give 1.5 g (75 percent) of aldehyde E-13 as a clear oil which was immediately used in the next step : 1H NMR (CDC13) 8 1.43 (dd, 2H, J=10), 1.78 (m, 2H), 2.31 (m, 1H), 2.91 (t, 2H, J=10. 6), 3.96 (m, 2H), 5.05 (s, 2H), 7.24 (m, 5H), 9.52 (s, 1H).
6.2 g With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 12 h; Reaction Step 2
Synthesis of benzyl 4-formylpiperidine-1-carboxylate
To a stirred solution of benzyl 4-(hydroxymethyl)piperidine-1-carboxylate (10.0 g, 40.2 mmol, 1.0 eq) in dichloromethane (150 ml), Dess-Martin periodinane (20.4 g, 48.2 mmol, 1.2 eq) was added at 0° C. and stirring was continued at room temperature for 12 h.
After completion of the reaction (monitored by TLC, 30percent ethyl acetate-hexane, Rf=0.45), the mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate solution, followed by brine.
The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure.
The crude product was purified by column chromatography on silica gel (100-200 mesh), eluting with a 30-40percent gradient of ethyl acetate in hexanes to obtain benzyl 4-formylpiperidine-1-carboxylate (6.2 g, 62.5percent). LCMS Purity: 78.54percent (ES+): m/z 248.27 (M+H+); tr=3.01 min.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2663 - 2666
[2] Patent: WO2007/93603, 2007, A1, . Location in patent: Page/Page column 15
[3] Patent: WO2014/22349, 2014, A1, . Location in patent: Paragraph 00158
[4] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 661 - 664
[5] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9830 - 9836
[6] Patent: WO2005/80394, 2005, A1, . Location in patent: Page/Page column 131-132
[7] European Journal of Organic Chemistry, 2008, # 25, p. 4277 - 4295
[8] Tetrahedron Letters, 2007, vol. 48, # 2, p. 199 - 202
[9] Patent: WO2014/70976, 2014, A1, . Location in patent: Page/Page column 20; 21
[10] Patent: US2015/252022, 2015, A1, . Location in patent: Paragraph 0375
[11] Patent: US2016/24056, 2016, A1, . Location in patent: Paragraph 0244
  • 2
  • [ 79-37-8 ]
  • [ 122860-33-7 ]
  • [ 138163-08-3 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane; dimethyl sulfoxide 26c.
Phenylmethyl 4-formylpiperidinecarboxylate
To a stirred solution of oxalyl chloride (2M solution in dichloromethane, 10.9 mL, 21.9 mmol) was added DMSO (3.1 mL, 3.4 g, 43.8 mmol) in dichloromethane (6 mL) over a period of 15 minutes.
The product of Example 26b (4.4 g, 17.5 mmol) in dichloromethane (7 mL) was then added at -78° C. over a period of 15 minutes.
The resultant solution was stirred at -78° C. for 1 hour and then triethylamine (12.2 mL, 8.86 g, 87.5 mmol) was added, dropwise, over a period of 15minutes.
The mixture was further stirred at -78° C. for 30 min and then at 0° C. for 15 min.
The reaction mixture was quenched with water and extracted with dichloromethane.
The combined organic phase was washed with 1percent HCl, water, dried over sodium sulfate, filtered and evaporated to give the title compound (4.4 g, 100percent) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ9.65 (s, 1H), 7.28-7.38 (m, 5H), 5.12 (s, 2H), 4.04 (br d, J=13.1 Hz, 2H), 2.97-3.06 (m, 2H), 2.38-2.45 (m, 1H), 1.88-1.92 (m,2H), 1.52-1.64 (m, 2H).
13C NMR (75 MHz, CDCl3) δ202.7, 155.2, 136.7, 128.5, 128.6, 127.9, 67.2, 47.8, 43.0, 25.1. LRMS (APIMS) m/z 248 (MH+).
Reference: [1] Patent: US2003/203915, 2003, A1,
  • 3
  • [ 87413-09-0 ]
  • [ 122860-33-7 ]
  • [ 138163-08-3 ]
Reference: [1] Patent: US6265434, 2001, B1,
  • 4
  • [ 6457-49-4 ]
  • [ 501-53-1 ]
  • [ 122860-33-7 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine In dichloromethane at 0 - 20℃; for 2 h; Example 24.; N-Benzyloxycarbonyl-4- (hydroxymethyl) piperidine (E-12);. A stirred solution of 4-hydroxymethylpiperidine (2.0 g, 17.4 mmol) in dry dichloromethane (DCM, 100 mL) was cooled to 0°C, treated with triethylamine (4.8 mL, 34.8 mmol) followed by benzyl chloroformate (3.7 mL, 34.8 mmol), allowed to warm to room temperature and stirred for two hours. The mixture was partitioned between DCM (50 mL) and water (30 mL). The layers were separated and the aqueous phase was extracted with DCM (2 x 50 mL). The combined organic phases were washed with brine (1 x 30 mL), dried over Na2S04 and evaporated to a residue, that was purified by column chromatography using a gradient of 70 to 100 percent EtOAc in hexanes as eluant to give 3.85 g (89 percent) of E-12 as clear oil : 1H NMR (CDC13) S 1. 17 (m, 2H), 1.72 (m, 3H), 2.15 (br s, 1H), 2. 78 (t, 2H, J=12. 24), 3.47 (d, 2H, J=6. 04), 4.20 (d, 2H, J=11. 68), 5.12 (s, 2H), 7.33 (m, 5H).
89% With triethylamine In dichloromethane at 0 - 20℃; To a stirred solution of 4-hydroxymethylpiperidine (1.0 g, 8.7 mmol, 1.0 equiv) in dry CH2Cl2 (50 mL) was added Et3N (2.4 mL, 17.4 mmol, 2.0 equiv) and benzylchoroformate (1.85 niL, 17.4 mmol, 2.0 equiv) at 0 "C. The mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was washed with water (20 mL) and the aqueous phase was extracted with CH2Cl2 (2 x 25 mL). The combined organic phases were washed with brine (15mL), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel to afford compound 64-a (1.95 g, 89percent) as a clear oil: 1H NMR (400 MHz, CDCl3) δ 5.10 (s, 2H), 4.20 (br d, J= 11.2 Hz, 2H), 3.48 (d, J= 6.4 Hz, 2H), 2.77 (t, J= 12.8 Hz, 2H), 1.62-1.70 (m, 3H), 1.10-1.20 (m, 2H).
42% With triethanolamine In dichloromethane Step B
Preparation of benzyl 4-(hydroxymethyl)-1-piperidinecarboxylate
Dissolved the amine (5.0 g, 45.8 mmol) from Step A in CH2Cl2 (50 ml) with TEA (22.5 ml, 158.6 mmol) and cooled to 0° C., then added benzyl chloroformate (10.4 ml, 73.3 mmol)and stirred at room temperature ca. 24 hr.
Extracted CH2Cl2 versus saturated NaHCO3and combined the organic layers, dried on MgSO4, filtered and evaporated.
Purified by flash chromatography to yield the pure title compound (3.34 g, 42percent).
MS (APCI) (M+H)+=250
Reference: [1] Patent: WO2005/80394, 2005, A1, . Location in patent: Page/Page column 131
[2] European Journal of Organic Chemistry, 2008, # 25, p. 4277 - 4295
[3] Patent: WO2010/46780, 2010, A2, . Location in patent: Page/Page column 63-64
[4] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8110 - 8113
[5] Patent: US2003/55244, 2003, A1,
[6] Patent: US5719303, 1998, A,
[7] Patent: US2007/54896, 2007, A1, . Location in patent: Page/Page column 24
[8] Synthesis, 2011, # 22, p. 3669 - 3674
[9] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 661 - 664
[10] Patent: WO2014/70976, 2014, A1, . Location in patent: Page/Page column 20
  • 5
  • [ 160809-38-1 ]
  • [ 122860-33-7 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 5℃; for 1 h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran
Example 2; 4-Hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (2); Piperidine-1 ,4-dicarboxylic acid 1 -benzyl ester 4-ethyl ester (1 ) (165 g, 567. mmol) was dissolved in tetrahydrofuran (1500 ml_) and cooled to 00C. Lithium aluminium hydride (311 ml_, 1 M in THF) was added dropwise maintaining the temperature below 5°C. The reaction mixture was stirred for one hour and aqueous sodium hydroxide (4 N) was added dropwise. The mixture was filtered and the filtercake was washed with diethyl ether. The organic layer was concentrated and dissolved in ethyl acetate, washed with water and brine, dried over sodium sulphate, filtered and concentrated to give 4-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (120 g, 85percent) as a yellow oil.
Reference: [1] Patent: WO2007/93603, 2007, A1, . Location in patent: Page/Page column 15
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2663 - 2666
[3] Tetrahedron Letters, 2007, vol. 48, # 2, p. 199 - 202
  • 6
  • [ 6457-49-4 ]
  • [ 13139-17-8 ]
  • [ 122860-33-7 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 1 h; Piperidin-4-ylmethanol (5.2 g, 45.1 mmol) was dissolved in 60 mE of THF and 60 mE of saturated NaHCO3 aq and then benzyl (2,5-dioxopyrrolidin- 1 -yl) carbonate (11.25 g, 45.1 mmol) added portionwise. The mixture was stirred for 1 h at RT, partitioned between AcOEt and water, washed twice with 1M HClaq and saturated NaClaq. Organic layer was dried over Na2504, evaporated under reduced pressure to afford the title compound (10.77 g, 43.2 mmol, 96percent yield). The product obtained was used in the following steps without thrther purifications. UPLC-MS: 0.80 mm, 250.2 [M+H]+, method 1.
Reference: [1] Patent: US2016/235734, 2016, A1, . Location in patent: Paragraph 0706; 0707; 0708
  • 7
  • [ 6457-49-4 ]
  • [ 1885-14-9 ]
  • [ 122860-33-7 ]
YieldReaction ConditionsOperation in experiment
44% With triethylamine In dichloromethane a)
1-Benzyloxycarbonyl-4-hydroxymethyl-piperidine.
A solution of 4-hydroxymethyl-piperidine (1.0g, 8.7 mmol) in dichloromethane (20ml) was treated triethylamine (1.3ml, 9.6 mmol) then benzylchloroformate (1.4ml, 9.6 mmol).
After 14h the reaction mixture was diluted with dichloromethane and washed with dilute aqueous sodium bicarbonate solution.
The organic extract was dried and evaporated.
Chromatography on silica eluding with 1:1 ethyl acetate:hexane afforded the product as a clear oil (0.97g, 44percent).
Reference: [1] Patent: EP1051413, 2003, B1,
  • 8
  • [ 501-53-1 ]
  • [ 122860-33-7 ]
Reference: [1] Patent: US2003/203915, 2003, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2663 - 2666
  • 9
  • [ 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,
  • 10
  • [ 10314-98-4 ]
  • [ 122860-33-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3586 - 3604
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9830 - 9836
  • 11
  • [ 6457-49-4 ]
  • [ 31139-36-3 ]
  • [ 122860-33-7 ]
Reference: [1] Patent: US4968704, 1990, A,
  • 12
  • [ 1126-09-6 ]
  • [ 122860-33-7 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 2, p. 199 - 202
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2663 - 2666
  • 13
  • [ 498-94-2 ]
  • [ 122860-33-7 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 661 - 664
  • 14
  • [ 122860-33-7 ]
  • [ 159275-17-9 ]
YieldReaction ConditionsOperation in experiment
10 g With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 3 h; Inert atmosphere To a 500 ml three neck round bottomed flask under nitrogen atmosphere, benzyl 4- (hydroxymethyl) piperidine- l-carboxylate (10 g, 40.1 1 mmol) was dissolved in CH2CI2 (100 ml) and cooled to 0 °C. Triphenyl phosphine (13.7 g, 52.14 mmol) in CH2CI2 (50 ml) was added to the reaction mixture and stirred at 0 °C for 20 minutes. Carbon tetra bromide (16 g, 48.13 mmol) in CH2CI2 (50 ml) was added to reaction mixture which was stirred at rt for 3 h. The reaction mixture was diluted with CH2CI2 and washed with water. Organic layer was dried over sodium sulfate and concentrated under vacuum and purified by column chromatography to give 10 g of benzyl 4-(bromomethyl) piperidine- l-carboxylate.
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3586 - 3604
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 13, p. 2606 - 2620
[3] Patent: WO2015/195950, , A1, . Location in patent: Page/Page column 82[3] Patent: , 2015, , . Location in patent: Page/Page column 82
  • 15
  • [ 558-13-4 ]
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  • [ 159275-17-9 ]
Reference: [1] Patent: US6562828, 2003, B1,
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