Home Cart 0 Sign in  

[ CAS No. 165530-45-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 165530-45-0
Chemical Structure| 165530-45-0
Structure of 165530-45-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 165530-45-0 ]

Related Doc. of [ 165530-45-0 ]

Alternatived Products of [ 165530-45-0 ]

Product Details of [ 165530-45-0 ]

CAS No. :165530-45-0 MDL No. :MFCD10697871
Formula : C12H23ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YRYNLXXXMXAVKV-UHFFFAOYSA-N
M.W : 262.78 Pubchem ID :53412057
Synonyms :

Calculated chemistry of [ 165530-45-0 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 77.81
TPSA : 32.78 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) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.29
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 1.73
Consensus Log Po/w : 2.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.25
Solubility : 1.47 mg/ml ; 0.00561 mol/l
Class : Soluble
Log S (Ali) : -2.18
Solubility : 1.74 mg/ml ; 0.00661 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.4
Solubility : 1.06 mg/ml ; 0.00403 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.58

Safety of [ 165530-45-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501 UN#:1760
Hazard Statements:H302-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 165530-45-0 ]

* 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 [ 165530-45-0 ]

[ 165530-45-0 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 405939-84-6 ]
  • [ 165530-45-0 ]
  • 4-{3-[<i>tert</i>-butoxycarbonyl-(5-{6-[<i>tert</i>-butoxycarbonyl-(3-chloro-phenyl)-amino]-pyrazin-2-yl}-pyridin-3-yl)-amino]-propyl}-piperazine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 2
  • 1-(3-chloropropyl)piperazine hydrochloride [ No CAS ]
  • [ 24424-99-5 ]
  • [ 165530-45-0 ]
  • 3
  • [ 165530-45-0 ]
  • N-(3-chlorophenyl)-6-[5-[[3-(1-piperazinyl)propyl]amino]-3-pyridinyl]-2-pyrazinamine [ No CAS ]
  • 4
  • [ 109-70-6 ]
  • [ 57260-71-6 ]
  • [ 165530-45-0 ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate; sodium iodide; In acetonitrile; at 20℃; Compound II-5b (20.24 g, 101.06 mmol) was dissolved in acetonitrile (200 mL) and 1-bromo-3-chloropropane (39.77 g, 252.65 mmol, 2.5 eq), potassium carbonate (13.97 g, 110.78 mmol) Sodium iodide (15.15 g, 101.06 mmol) was added and stirred overnight at room temperature. After the reaction was completed, the reaction solvent was concentrated under reduced pressure, ethyl acetate, distilled water and brine were sequentially washed, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (dichloromethane: methanol = 20: 1-> 15: 1 volume ratio mixture gradient elution) to give the title compound II-5c (22.93 g, 82%).
77.4% Mixing 1-piperazincarboxylic acid tert-butyl ester (2.00 g, 10.7 mmol) in 25 mL of anhydrous DMF and anhydrous THF (1:1)Sodium hydride (0.27 g, 11.3 mmol) and anhydrous lithium bromide (0.57 g, 6.6 mmol) were gradually added at 0 C under argon, and stirred at 0 C for 4 h.1-Bromo-2-chloropropane (1.84 g, 11.8 mmol) was added dropwise.The reaction was transferred to room temperature 25 C and stirred at 0 C for 5 h. The reaction was completed, and concentrated under reduced pressure. The mixture was evaporated to dryness. The mixture was evaporated to dryness. The organic layer was concentrated under reduced pressure, and the obtained crude product was purified by column chromatography on silica gel (200-300 mesh), and a mixture of dichloromethane and methanol (V:V=30:1) as eluent.Intermediate d, yellow white solid 2.18g, yield 77.4%,
67% With sodium hydroxide; In water; acetone; at 20℃; for 3h;Inert atmosphere; Tert-butyl piperazine-1-carboxylate (5 g, 26.8 mmol), 5 M aqueous NaOH (6.44 mL, 32.2 mmol) and 1-bromo-3-chloropropane (2.65 mL, 26.8 mmol) were stirred together in acetone (100 mL) under anitrogen atmosphere at room temperature for 3 h. The solvent was removed in vacuo and diluted withwater (70 mL). The aqueous was extracted with DCM (3 x 70 mL) and the combined organic layerswere passed through a hydrophobic frit and the solvent was removed in vacuo to afford tert-butyl 4-(3-chloropropyl)piperazine-1-carboxylate (4.731 g, 18.00 mmol, 67 % yield) as a colourless oil. Rf =0.33, 50 % EtOAc in cyclohexane; νmax (neat): 2933, 2611, 1691, 1166, 1122, 1004 cm1; 1H NMR (400MHz, CDCl3) δ = 3.62 (2H, t, J = 6.5 Hz), 3.45 (4H, t, J = 5.1 Hz), 3.04 - 3.10 (1H, m), 2.52 (2H, t, J = 7.1Hz), 2.41 (4H, t, J = 5.1 Hz), 1.97 (2H, quin, J = 6.8 Hz), 1.47 (9H, s); 13C NMR (101 MHz, CDCl3) δ = 154.7, 79.6, 55.4 (2C), 53.0, 43.0 (3C), 29.7, 28.4 (3C); HRMS: (C12H23ClN2O2) [M+H]+ requires 263.1534, found[M+H]+ 263.1523.
50% With triethylamine; In dichloromethane; at 20℃; for 48h;Inert atmosphere; 1-Boc-piperazine (1.01 g, 5.24 mmol), and triethylamine(0.90 mL, 6.50 mmol) were dissolved in dichloromethane (10 mL).1-Bromo-3-chloropropane (0.64 mL, 6.50 mmol) was added andthe reaction mixture stirred at room temperature for 2 days. Thereaction mixturewas washed with water (10 mL) followed by brine(10 mL). The organic phase was dried over magnesium sulfate andconcentrated under reduced pressure to afford a white residue. Thisresidue was purified by column chromatography (20e100% ethylacetate in petroleum spirits 40-60 C) to afford the desired productas a pale yellow oil (0.70 g, 50%). 1H NMR (CDCl3) d 3.59 (2H, t, J 6.6 Hz), 3.42 (4H, apparent t), 2.48 (2H, t, J 7.0 Hz), 2.37 (4H,apparent t),1.97e1.90 (2H, m),1.45 (9H, s); 13C NMR (CDCl3) d 154.8,79.7, 55.5, 53.1, 43.2, 29.9, 28.5.
With triethylamine; In dichloromethane; at 50℃; for 3h; To a solution of N-Boc-piperazine (2 g) in [CH2CL2] (40 ml) and TEA (1.8 ml), cooled at [0 C, 3-CHLORO-1-BROMOPROPANE] (1.3 ml) was added and the solution was heated at 50 [C] for 3 hours. The solvent was evaporated at reduced pressure and the residue was dissolved in CH2C12 and washed with water. The organic phase was dried over [NA2SO4] and filtered, the solvent evaporated at reduced pressure and the crude product was purified by chromatography on silica gel eluting with ethyl acetate/hexane (8/2 v/v) to obtain [N'- (3-CHLOROPROPYL)-N-BOC-PIPERAZINE] (1.7 g). [N'- (3-CHLOROPROPYL)-N-BOC-PIPERAZINE] was dissolved in [HCL/ETHYL] acetate (10 ml), the solution was cooled at [0 C] in an ice bath and stirred for 1 hour at [0 C] then it is left to return to room temperature. The solvent was eliminated and the residue was treated with diethyl ether and the obtained solid product was filtered and used without any further purification..
With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 50℃; for 3.01667h; To a solution of 4.94 g tert-Butyl-1-piperazine-carboxylate and 12.66 g 1-Bromo-3- chloropropane in 15 ml DMF (dry) was added 4.08 g K2CO3 and the reaction heated to 50 0C for one minute and stirred at room temperature for additional 3 h. The reaction mixture is pored into 200 ml of water and extracted with DCM. The combined organic phases were washed with water and dried over MgSO4 and evaporated in vacuo. The product was purified by flash column chromatography (n-heptane/ethylacetate 1 :1, RF = 0.3) Yield 3.9 g.
With triethylamine; In acetonitrile; at 50℃; for 0.333333h;Microwave irradiation; Preparation of tert-Butyl 4-(3-chloropropyl)piperazine-l-carboxylateieri-Butylpiperazine-l-carboxylate (500 mg, 2.68 mmol) was dissolved in acetonitrile (20 ml) and l-bromo-3-chloropropane (423 mg, 2.68 mmol) and triethylamine (272 mg, 2.68 mmol) added. The mixture was put in 5 x 10 rriL microwave tubes and each heated at 50 C for 20 mins . Combined the tubes and evaporated to dryness. Dissolved in the minimum quantity of dichloromethane and purified by chromatography on silica gel (50 g column eluting with 10-100% EtOAc -petrol gradient over 20CV at 85 mL/min. Appropriate fractions were identified by UV and permanganate visualized TLC (silica plate) and evaporated to give the product as a pale yellow oil (366 mg, 52%)..H NMR (300 MHz, d6-CDCl3): δ 1.43 (9H, s, C(CH3)3), 1.87 - 1.97 (2H, m, CH2CH2), 2.35 (4H, t, J = 5.0 Hz, pip-CH2), 2.46 (24H, t, J = 7.0 Hz, N-CH2), 3.40(4H, t, J = 5.0 Hz, pip-CH2) and 3.58 (2H, t, J = 6.5 Hz, CH2-C1). 13C NMR (75 MHz, d6-CDCl3): δ 28.4 (C(CH3)3), 29.7 (CH2CH2CH2), 43.0 (CH2-C1), 43.8 (pip- CH2), 53.0 (N-CH2), 55.3 (pip-CH2), 79.6 (C(CH3)3) and 154.7 (C=0).
11.77 g With sodium carbonate; In dichloromethane; at 20℃; 1-Boc-4-(3-mercaptopropanyl)piperazine [0385] To a suspension of piperizaine (30.00 g, 348.27 mmol) and sodium carbonate (106 g, 348.27 mmol) in dichloromethane (200 ml) was added dropwise a solution of Di- tert-butyl dicarbonate (18.98 g, 87.07 mmol) in dichloromethane (30 ml) at room temperature for one hour. Then the mixture was stirred at room temperature overnight. The mixture was mixed with water (100 ml) and separated. The dichloromethane layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was dissolved in dichloromethane (100 ml). Sodium carbonate (15.44 g, 145.70 mmol) and 1- bromo-3-chloropropane (15.29 g, 97.13 mmol) were added. The mixture was stirred at room temperature overnight. The mixture was mixed with water (80 ml) and separated. The dichloromethane layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using hexane and ethyl acetate as eluent to give 11.77 g of l-Boc-4-(3-chloropropanyl)piperazine.
With potassium carbonate; sodium iodide; In acetonitrile; at 20℃; for 24h; To a stirred solution of tert-butyl piperazine-1-carboxylate (1.1) (10 g, 53.7 mmol) in acetonitrile (125 mL) was added 1-bromo-3-chloropropane (21.13 g, 134.2 mmol, 2.5 eq), potassium carbonate (7.4 g, 53.7 mmol, leq) and sodium iodide (8.05 g, 53.7 mmol, 1 eq). The mixture was stirred for 24h at room temperature and the solvent was evaporated. The residue was solubilised again in CH2CI2 and basified with 1 M NaOHsolution. Two layers were separated and the aqueous layer was extracted three times with CH2CI2. The combined organic layer was dried with MgSO4 and evaporated under reduced pressure to give the compound 1.2 with a good purity, which was directly used for the next step without purification. MALDI-TOF m/z263.10-265.14 [M+H]
With potassium carbonate; sodium iodide; In acetonitrile; at 20℃; for 24h; To a stirred solution of ierf-butyl piperazine-1 -carboxylate (1.1 ) (10 g, 53.7 mmol) in acetonitrile (125 ml_) was added 1 -bromo-3-chloropropane (21 .13 g, 134.2 mmol, 2.5 eq), potassium carbonate (7.4 g, 53.7 mmol, 1 eq) and sodium iodide (8.05 g, 53.7 mmol, 1 eq). The mixture was stirred for 24h at room temperature and the solvent was evaporated. The residue was solubilised again in CH2CI2 and basified with 1 M NaOH solution. Two layers were separated and the aqueous layer was extracted three times with CH2CI2. The combined organic layer was dried with MgS04 and evaporated under reduced pressure to give the compound 1.2 with a good purity, which was directly used for the next step without purification. MALDI-TOF m/z 263.1 0-265.14 [M+H]+

  • 5
  • [ 165530-45-0 ]
  • 1-(3-chloropropyl)piperazine dihydrochloride salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride; In water; ethyl acetate; 1-(3-chloropropyl)-4-(t-butyloxycarbonyl)-piperaxine (4.0 g, 15.2 mmol) was treated with hydrochloric acid in ethyl acetate to obtain Compound-5 (3.17 g, 13.5 mmol) in yield 89%. 1H NMR (400 MHz, D2O, δ): 3.63-3.54 (m, 9H), 3.39 (s, 1H), 3.40-3.35 (m, 2H), 2.21-2.14 (m, 2H). 13C NMR (100.6 MHz, D2O, δ): 54.8, 48.6, 41.1, 40.7, 26.2. IR (KBr): 3356, 3001, 1443, 1301, 1160, 1084 cm-1 MS m/z: 162.1 (M+, 13.6), 120.1 (100.0), 99.1 (79.5), 70.1 (29.2), 56.1 (49.6). HRMS-EI (m/z): [M]+ calculated for, C7H15ClN2, 162.0924. found, 162.0930.
89% With hydrochloric acid ethyl acetate; In ethyl acetate; The 1 - (3-chloro-propyl) - 4 - (tert butoxy carbonyl)-piperazine (4.0g, 15 . 2mmol) dissolved in ethyl acetate to get after processing hydrochloric acid of 1 - (3-chloro-propyl)-piperazine · hydrochloride (3.17g, 13 . 5mmol), yield 89%.
89% With hydrogenchloride; In ethyl acetate; 1-(3-chloropropyl)-4-(t-butyloxycarbonyl)-piperaxine (4.0 g, 15.2 mmol) was treated with hydrochloric acid in ethyl acetate to obtain Compound-5 (3.17 g, 13.5 mmol) in yield 89%. 1H NMR (400 MHz, D2O, δ): 3.63-3.54 (m, 9H), 3.39 (s, 1H), 3.40-3.35 (m, 2H), 2.21-2.14 (m, 2H). 13C NMR (100.6 MHz, D2O, δ): 54.8, 48.6, 41.1, 40.7, 26.2. IR (KBr): 3356, 3001, 1443, 1301, 1160, 1084 cm-1 MS nil: 162.1 (M+, 13.6), 120.1 (100.0). 99.1 (79.5), 70.1 (29.2), 56.1 (49.6). HRMS-EI (m/z): [M]+ calculated for, C7H15ClN2, 162.0924; found, 162.0930.
With hydrogenchloride; In ethyl acetate; at 0 - 20℃; To a solution of N-Boc-piperazine (2 g) in [CH2CL2] (40 ml) and TEA (1.8 ml), cooled at [0 C, 3-CHLORO-1-BROMOPROPANE] (1.3 ml) was added and the solution was heated at 50 [C] for 3 hours. The solvent was evaporated at reduced pressure and the residue was dissolved in CH2C12 and washed with water. The organic phase was dried over [NA2SO4] and filtered, the solvent evaporated at reduced pressure and the crude product was purified by chromatography on silica gel eluting with ethyl acetate/hexane (8/2 v/v) to obtain [N'- (3-CHLOROPROPYL)-N-BOC-PIPERAZINE] (1.7 g). [N'- (3-CHLOROPROPYL)-N-BOC-PIPERAZINE] was dissolved in [HCL/ETHYL] acetate (10 ml), the solution was cooled at [0 C] in an ice bath and stirred for 1 hour at [0 C] then it is left to return to room temperature. The solvent was eliminated and the residue was treated with diethyl ether and the obtained solid product was filtered and used without any further purification..

  • 6
  • [ 6940-76-7 ]
  • [ 57260-71-6 ]
  • [ 165530-45-0 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h; A mixture of f-butyl 1-piperazinecarboxylate (0.500 g, 2.68 mmol, Lancaster), 1-chloro-3-iodopropane (1.10 g, 5.36 mmol, Aldrich) and K2C03 (1.85 g, 13.4 mmol) in 20 mL of anhydrous DMF was stirred at RT. After 18 hours the solution was diluted with water and the resulting mixture extracted with EtOAc (3x). The combined extracts were washed with saturated aqueous brine (2x), dried over Na2S04, and concentrated at reduced pressure. The crude product was purified by flash chromatography (silica gel, hexane/EtOAc) to afford 0.339 g (48%) of f-butyl 4-(3-chloropropyl)-1-piperazinecarboxylate as a yellow oil. 1H NMR (DMSO-cf6): 8 3.70 (t, 2H), 3.32 (m, 4H), 2.43 (t, 2H), 2.34 (m, 4H), 1.90 (m, 2H), 1.42 (s, 9H).
  • 7
  • [ 165530-45-0 ]
  • [ 946517-70-0 ]
YieldReaction ConditionsOperation in experiment
With sodium azide; In dimethyl sulfoxide; at 90℃; for 15h; Tert-Butyl-4-(3-Chloropropyl)-1-piperazine carboxylate and sodium-azide were dissolved (suspended) in 8 ml DMSO dry and heated to 9O0C for 15 h. The reaction mixture was allowed to cool to room temperature and pored into 50 ml of water. The product was extracted with DCM and the combined organic phases dried over MgSO4. The product was purified by flash column chromatography (n-heptane/ethylacetate 1 :1 , RF = 0.34). Yield: 3.5 g.
  • 8
  • [ 165530-45-0 ]
  • [ 149-30-4 ]
  • [ 1351411-55-6 ]
YieldReaction ConditionsOperation in experiment
64% With potassium carbonate;potassium iodide; In acetone; for 18h;Reflux; Preparation of tert-Butyl 4-(3-(benzo[d]thiazol-2-ylthio)propyl)piperazine-l- carboxylateBenzo[d]thiazole-2-thiol (233 mg, 1.393 mmol) and tert-butyl 4-(3- chloropropyl)piperazine-l-carboxylate (366 mg, 1.393 mmol) were dissolved in acetone (40 ml) and potassium carbonate (386 mg, 2 equivs) and one small crystal of potassium iodide (catalytic) added. The vigorously stirred suspension was heated at reflux for 18 h . TLC (1 : 1 ethyl acetate: petrol) showed one major spot at ~Rf 0.5. Evaporated, partitioned between water (15 mL) and dichloromethane (25 mL) separated with a phase separator and evaporated. The product was purified by chromatography on silica gel (50 g cartridge) eluting with 5-100% ethyl acetate - petrol over 16CV to give the product as a viscous oil (350 mg, 64%). LCMS calcd for C19H27N302S2: 393.2; found:394.1 [M+H]+ in ES+..H NMR (300 MHz, CDCI3): δ 1.45 (9H, s, tBu), 1.97-2.06 (1H, m, CH2-CH2), 2.34 -2.32 (4H, pip-CH2), 2.50 (2H, t, J = 7.0 Hz, CH2-N), 3.39 (2H, t, J = 7.5Hz, C¾-N),3.40-3.46 (4H, m, pip-CH2), 7.24 - 7.31 (1H, m, benzo-C5/6-H), 7.36-7.43 (1H, m, benzo-C5/6-H), 7.74 (1H, d, J = 8.0 Hz, benzoC4-H) and 7.83 (1H, d, J = 7.5 Hz, benzoC7-H). 13C NMR (75 MHz, CDCI3): δ 26.7 (CH2CH2CH2), 28.6 (C(CH3)3),31.1 (CH2- S), 31.6 (pip-CH2), 53.1(C¾-N), 57.1(pip-CH2), 79.8 (C-O), 121.1(benzoC7), 121.6 (benzoC-4), 124.3 (benzoC6), 12126.2 (benzoC-5), 135.4 (C-S), 153.5 (C-N), 154.9 (C=0) and 167.2 (S-C=N).
  • 9
  • [ 165530-45-0 ]
  • [ 1351412-04-8 ]
  • 10
  • [ 165530-45-0 ]
  • [ 1351412-05-9 ]
  • 11
  • [ 165530-45-0 ]
  • [ 1351411-56-7 ]
  • 12
  • [ 165530-45-0 ]
  • [ 1351411-57-8 ]
  • 13
  • [ 165530-45-0 ]
  • [ 1351409-99-8 ]
  • 14
  • [ 165530-45-0 ]
  • [ 2010-06-2 ]
  • [ 1351412-03-7 ]
YieldReaction ConditionsOperation in experiment
29% With caesium carbonate; In N,N-dimethyl-formamide; at 90℃; for 16h; Preparation of tert-Butyl 4-(3-((4-phenylthiazol-2-yl)amino)propyl)piperazine-l- carboxylate To a solution of tert-butyl 4-(3-chloropropyl)piperazine-l -carboxylate (350 mg, 1.3 mmol) in dimethylformamide (10 mL) was added cesium carbonate (0.5 g, 1.5 mmol), and 2-amino-4-phenylthiazole (350mg, 2 mmol). The mixture was heated at 90 C for 16 hr. The reaction mixture was diluted in ethyl acetate (50 mL) and washed with water (50 mL) and brine (50 mL). The organics were dried over magnesium sulfate and concentrated. The residue diluted in dichloromethane (2 mL) and crude material was separated on silica (50 g) eluting with petrol/ethyl acetate (10% to 100% ethyl acetate over 14 CV at a flow of 40 mL/min). This gave the product as a yellow oil (150 mg, 29%).LCMS: calcd for C21H30N4O2S 402.2; found 403.2 [M+H] .
  • 15
  • [ 165530-45-0 ]
  • [ 17356-08-0 ]
  • C13H26N4O2S*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 4h;Reflux; [0386] To a solution of l-Boc-4-(3-chloropropanyl)piperazine (11.77 g, 44.90 mmol) in ethanol (100 ml) was added thiourea (6.82 g, 89.80 mmol). The mixture was heated to reflux for 4 hours. A solution of sodium hydroxide (2.69 g, 67.35 mmol) in water (40 ml) was added, and the mixture was continued to reflux for another 2 hours. Then most solvent was evaporated under reduced pressure. The residue was mixed with ethyl acetate (100 ml) and brine (50 ml) and separated. The ethyl acetate was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using hexane and acetone as eluent to give 7.5 g of tert-butyl 4-N-Boc-l-(3- mercaptopropanyl)piperazine.
  • 16
  • [ 24424-99-5 ]
  • [ 165530-45-0 ]
  • 17
  • [ 165530-45-0 ]
  • tert-butyl 4-N-Boc-1-(3-mercaptopropanyl)piperazine [ No CAS ]
  • 18
  • [ 165530-45-0 ]
  • octyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 19
  • [ 165530-45-0 ]
  • nonyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 20
  • [ 165530-45-0 ]
  • decyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 21
  • [ 165530-45-0 ]
  • undecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 22
  • [ 165530-45-0 ]
  • dodecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 23
  • [ 165530-45-0 ]
  • tridecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 24
  • [ 165530-45-0 ]
  • tetradecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 25
  • [ 165530-45-0 ]
  • pentadecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 26
  • [ 165530-45-0 ]
  • hexadecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 27
  • [ 165530-45-0 ]
  • heptadecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 28
  • [ 165530-45-0 ]
  • octadecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 29
  • [ 165530-45-0 ]
  • nonadecyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 30
  • [ 165530-45-0 ]
  • icosyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 31
  • [ 165530-45-0 ]
  • methyl 5-(4-(3-chloropropyl)piperazin-1-yl)-5-oxopentanoate [ No CAS ]
  • 32
  • [ 165530-45-0 ]
  • methyl 6-(4-(3-chloropropyl)piperazin-1-yl)-6-oxohexanoate [ No CAS ]
  • 33
  • [ 165530-45-0 ]
  • methyl 7-(4-(3-chloropropyl)piperazin-1-yl)-7-oxoheptanoate [ No CAS ]
  • 34
  • [ 165530-45-0 ]
  • methyl 8-(4-(3-chloropropyl)piperazin-1-yl)-8-oxooctanoate [ No CAS ]
  • 35
  • [ 165530-45-0 ]
  • methyl 9-(4-(3-chloropropyl)piperazin-1-yl)-9-oxononanoate [ No CAS ]
  • 36
  • [ 165530-45-0 ]
  • methyl 5-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-5-oxopentanoate [ No CAS ]
  • 37
  • [ 165530-45-0 ]
  • methyl 6-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-6-oxohexanoate [ No CAS ]
  • 38
  • [ 165530-45-0 ]
  • methyl 7-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-7-oxoheptanoate [ No CAS ]
  • 39
  • [ 165530-45-0 ]
  • methyl 8-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-8-oxooctanoate [ No CAS ]
  • 40
  • [ 165530-45-0 ]
  • methyl 9-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-9-oxononanoate [ No CAS ]
  • 41
  • [ 165530-45-0 ]
  • ethyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 42
  • [ 165530-45-0 ]
  • propyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 43
  • [ 165530-45-0 ]
  • butyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 44
  • [ 165530-45-0 ]
  • pentyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 45
  • [ 165530-45-0 ]
  • hexyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 46
  • [ 165530-45-0 ]
  • heptyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 47
  • [ 165530-45-0 ]
  • octyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 48
  • [ 165530-45-0 ]
  • nonyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 49
  • [ 165530-45-0 ]
  • decyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 50
  • [ 165530-45-0 ]
  • undecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 51
  • [ 165530-45-0 ]
  • dodecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 52
  • [ 165530-45-0 ]
  • tridecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 53
  • [ 165530-45-0 ]
  • tetradecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 54
  • [ 165530-45-0 ]
  • pentadecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 55
  • [ 165530-45-0 ]
  • hexadecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 56
  • [ 165530-45-0 ]
  • heptadecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 57
  • [ 165530-45-0 ]
  • octadecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 58
  • [ 165530-45-0 ]
  • nonadecyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 59
  • [ 165530-45-0 ]
  • icosyl 4-(4-(3-chloropropyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 60
  • [ 165530-45-0 ]
  • ethyl 4-(4-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 61
  • [ 165530-45-0 ]
  • propyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 62
  • [ 165530-45-0 ]
  • butyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 63
  • [ 165530-45-0 ]
  • pentyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 64
  • [ 165530-45-0 ]
  • hexyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 65
  • [ 165530-45-0 ]
  • heptyl 4-(4-(3-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yloxy)propyl)piperazin-1-yl)-4-oxobutanoate [ No CAS ]
  • 66
  • [ 165530-45-0 ]
  • N,N-diisobutyl-3-(piperazin-1-yl)propylamine [ No CAS ]
  • 67
  • [ 165530-45-0 ]
  • N,N-diisobutyl-3-(4-(3-chloropropyl)piperazin-1-yl)propylamine [ No CAS ]
  • 68
  • [ 165530-45-0 ]
  • ethyl 5-(3-(4-(3-(N,N-diisobutylamino)propyl)piperazin-1-yl)propyl)-8-methyl-1,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-2-carboxylate [ No CAS ]
  • 69
  • [ 165530-45-0 ]
  • 1-(3-(2-propyl-1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)propyl)piperazine trihydrochloride [ No CAS ]
  • 70
  • [ 165530-45-0 ]
  • C18H39N3O [ No CAS ]
  • 71
  • [ 165530-45-0 ]
  • 1-[2-(piperidin-1-yl)ethyl]-4-(3-(2-propyl-1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)propyl)piperazine [ No CAS ]
  • 72
  • [ 165530-45-0 ]
  • [ 18144-32-6 ]
  • tert-butyl 4-(3-(2-propyl-1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)propyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% To a solution of 2-propyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 2.8a (1.50 g, 7.0 mmol) in THF (20 mL) at 000 was added sodium hydride (0.67 g, 28.0 mmol). The solution was stirred for 30 mn and tert-butyl 4-(3-chloropropyl)piperazine-1 -carboxylate1.2 (2.02 g, 7.7 mmol) added. After refluxing for 24h, the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (CH2CI2/MeOH: 95/5) gave the compound 2.13a. Yield 76%. 1H NMR (300 MHz, ODd3) 6 = 1.12 (t, 3H, J= 7.4 Hz), 1.60 (5, 9H), 1.83 (m, 2H), 2.05 (m, 2H), 2.45 (m, 6H), 2.80 (t, 2H, J= 7.8 Hz), 2.95-3.10 (m, 4H), 3.60 (m, 4H), 3.92 (5, 2H), 4.20 (t, 2H,J= 6.8 Hz), 7.22 (t, 1H, J= 7.1 Hz), 7.30 (t, 1H, J= 8.1 Hz), 7.50 (d, 1H, J= 8.1 Hz), 7.62 (d, 1H, J= 7.6 Hz). LOMS m/z341.1 [M+H-Boc].
  • 73
  • [ 165530-45-0 ]
  • [ 110-96-3 ]
  • tert-butyl 4-(3-(N,N-diisobutylamino)propyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With N-ethyl-N,N-diisopropylamine; sodium iodide; for 24h;Reflux; To a stirred solution of tert-butyl 4-(3-chloropropyl)piperazine-1 -carboxylate (1.2) (11 .35 g, 43.3 mmol, 1 eq) in CH2CI2 (400 mL) was added the amine (5 eq), N,Ndiisopropylethylamine (5.6 g, 43.3 mmol, 1 eq) and sodium iodide (6.5 g, 43.3 mmol, leq). The mixture was warmed to reflux and stirred for 24h. The solvent was then evaporated. The residue was solubilised again in CH2CI2 and alkalinized with 1 M NaOHsolution. Two layers were separated and the aqueous layer was extracted three times with CH2CI2. The combined organic layer was dried with MgSO4 and evaporated under reduced pressure. The crude was purified by chromatography on silica gel (CH2CI2/MeO:95/5) to give the corresponding compounds 1.3.
With N-ethyl-N,N-diisopropylamine; sodium iodide;Reflux; General procedure: To a stirred solution of terf-butyl 4-(3-chloropropyl)piperazine-1 -carboxylate (1.2) (1 1 .35 g, 43.3 mmol, 1 eq) in CH2CI2 (400 ml_) was added the amine (5 eq), N,N- diisopropylethylamine (5.6 g, 43.3 mmol, 1 eq) and sodium iodide (6.5 g, 43.3 mmol, 1 eq). The mixture was warmed to reflux and stirred for 24h. The solvent was then evaporated. The residue was solubilised again in CH2CI2 and alkalinized with 1 M NaOH solution. Two layers were separated and the aqueous layer was extracted three times with CH2CI2. The combined organic layer was dried with MgSO4 and evaporated under reduced pressure. The crude was purified by chromatography on silica gel (CH2CI2/ eO:95/5) to give the corresponding compounds 1.3. The compound 1.3a was synthesized according to the procedure described by using NN-diisobutylamine (27.96 g, 5 eq). Yield: 73%. MALDI-TOF m/z356.30 [M+H]+
  • 74
  • [ 165530-45-0 ]
  • [ 126912-70-7 ]
  • tert-butyl 4-(3-(8-methoxy-1,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-2-yl)propyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With potassium carbonate; In acetonitrile; for 24h;Reflux; To a solution of 8-methoxy-1 H,2H,3H,4H,5H-pyrido[4,3-b]indole 2.4 (1 .3 g, 6.43 mmol)) in acetonitrile (20 mL) was added the tert-butyl 4-(3-chloropropyl)piperazine-1- carboxylate 1.2 (1.69 g, 6.43 mmol) and K2C03 (1.33 g, 9.64 mmol). After being stirredfor 24h at reflux, the mineral was filtered and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel or by preparative TLC (CH2CI2/MeOH: 90/10) gave the compound 2.9. Yield 49%. 1H NMR (300 MHz, CDCI3) 5=1.47 (s, 12H), 1.82 (m, 2H), 2.32-2.48 (m, 6H), 2.63 (m, 4H), 2.79 (t, 2H, J= 5.4 Hz), 3.42 (m, 4H),3.67 (s, 2H), 3.82 (s, 3H), 6.70 (dd, 1 H, J= 2.4 Hz, J=8.8 Hz), 6.83 (d, 1H, J= 2.4 Hz), 7.00 (d, 1H, J= 8.8 Hz), 8.75 (5, 1H). LCMS m/z429.1 [M+H].
  • 75
  • [ 165530-45-0 ]
  • [ 16502-01-5 ]
  • tert-butyl 4-(3-{1H,2H,3H,4H,9H-pyrido[3,4-b]indol-2-yl}propyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate; In acetonitrile; for 24h;Reflux; To a solution of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 2.6 (1.57 g, 9.13 mmol) in acetonitrile (20 mL) was added <strong>[165530-45-0]tert-butyl 4-(3-chloropropyl)piperazine-1-carboxylate</strong> 1.2 (2.00 g, 7.61 mmol) and K2C03 (1 .57 g, 11 .4 mmol). After being stirred for 24h at ref lux, the mineral was filtered and the solvent removed under reduced pressure. The crudeproduct was purified by column chromatography on silica gel or by preparative TLC(CH2CI2/MeOH: 90/10) gave the compound 2.11. Yield 82%. 1H NMR (300 MHz, CDCI3)5 1.48 (5, 12H), 1.82 (m, 2H), 2.32-2.49 (m, 6H), 2.62 (t, 2H, J 7.4 Hz), 2.85 (m, 4H),3.45 (m, 4H), 3.62 (s, 2H), 7.01 -7.20 (m, 2H), 7.25 (d, 1H, J= 8.3 Hz), 7.48 (d, 1H, J=8.3 Hz), 8.00 (s, 1 H). LCMS m/z400.1 [M+H].
  • 76
  • [ 165530-45-0 ]
  • 1-(3-(8-methoxy-1,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-2-yl)propyl)piperazine [ No CAS ]
  • 77
  • [ 165530-45-0 ]
  • N,N-diisobutyl-3-[4-(3-(1,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-2-yl)propyl)piperazin-1-yl]propylamine [ No CAS ]
  • 78
  • [ 165530-45-0 ]
  • C33H42N2O9S2 [ No CAS ]
  • 79
  • [ 165530-45-0 ]
  • 4β-((3-(piperazin-1-yl)propyl)disulfanyl)-4'-O-dimethyl-4-desoxypodophyllotoxin [ No CAS ]
  • 80
  • [ 165530-45-0 ]
  • 2,3-difluoro-5-(5-methyl-2-(pyrimidin-2-yl)-7,8-dihydropyrido [4,3-d]pyrimidin-6(5H)-yl)phenol [ No CAS ]
  • tert-butyl 4-[3-[2,3-difluoro-5-(5-methyl-2-pyrimidin-2-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)phenoxy]propyl]piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43 mg With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 110℃; for 10h; Example 108: tert-butyl 4-[3-[2,3-difluoro-5-(5-methyl-2-pyrimidin-2-yl-7,8-dihydro-5H- pyrido[4,3-d]pyrimidin-6-yl)phenoxy]propyl]piperazine-1-carboxylate A mixture of 2,3-difluoro-5-(5-methyl-2-pyrimidin-2-yl-7,8-dihydro-5H-pyrido[4,3- d]pyrimidin-6-yl)phenol (400 mg, 1.13 mmol), tert-butyl 4-(3-chloropropyl)-piperazine-1- carboxylate (887 mg, 3.38 mmol,), KI (187 mg, 1.13 mmol) and K2CO3 (467 mg, 3.38 mmol) in DMF (10 ml) was heated with stirring at 110 C for 10 hrs. The resulting mixture was concentrated in vacuo and the residue was purified by flash column to give a white solid (200 mg). The white solid was further purified by prep-HPLC to give tert-butyl 4-[3-[2,3-difluoro-5- (5-methyl-2-pyrimidin-2-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6- yl)phenoxy]propyl]piperazine-1-carboxylate (43 mg).1H NMR (400 MHz, CDCl3) δ: 9.05 (d, 2H), 8.79 (s, 1H), 7.39-7.52 (m, 1H), 6.33-6.47 (m, 2H), 4.90-5.03 (m, 1H), 4.06-4.17 (m, 2H), 3.67-3.78 (m, 1H), 3.39-3.58 (m, 5H), 3.20-3.38 (m, 2H), 2.50-2.62 (m, 2H), 2.35-2.49 (m, 4H), 1.94-2.09 (m, 2H), 1.38-1.54 (m, 12H). MS obsd. (ESI+) [(M+H)+]: 582.
  • 81
  • [ 165530-45-0 ]
  • 6-[3,4-difluoro-5-(3-piperazin-1-ylpropoxy)phenyl]-5-methyl-2-pyrimidin-2-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine hydrochloride [ No CAS ]
  • 82
  • [ 165530-45-0 ]
  • 1-[4-[3-[2,3-difluoro-5-(5-methyl-2-pyrimidin-2-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)phenoxy]propyl]piperazin-1-yl]ethanone [ No CAS ]
  • 83
  • [ 165530-45-0 ]
  • 6-[3,4-difluoro-5-[3-(4-methylsulfonylpiperazin-1-yl)propoxy]phenyl]-5-methyl-2-pyrimidin-2-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine [ No CAS ]
  • 84
  • [ 165530-45-0 ]
  • [ 666816-98-4 ]
  • C22H31BrN6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% 8-Bromo-7-[1-(2-butynyl)]-3-methyl-1H-2,6-dicarbonylindole (0.64 g, 3.5 mmol)Potassium carbonate (0.96 g, 6.9 mmol) was dissolved in 10 mL of NMP solvent, heated to 70 C and stirred for 15 min. 4-(3-Chloropropyl)piperazine-1-carboxylic acid tert-butyl ester d (1.00 g, 3.8 mmol) was gradually added and stirred at 70 C for 6 h. After the reaction was completed, it was cooled to room temperature (0 C.), and the mixture was stirred and evaporated to dryness. The obtained crude product was separated by silica gel (300-400 mesh) column chromatography, and the mixture of dichloromethane-methanol (V:V=30:1) was used as an eluent to obtain intermediate b, 1.71 g of a yellow solid, yield of 86.0%.
  • 85
  • [ 165530-45-0 ]
  • [ 205448-31-3 ]
  • tert-butyl 4-(3-((4-chloro-6-methoxyquinolin-7-yl)oxy)propyl)piperazine-1-carboxylate [ No CAS ]
Same Skeleton Products
Historical Records

Related Parent Nucleus of
[ 165530-45-0 ]

Piperazines

Chemical Structure| 1374975-96-8

[ 1374975-96-8 ]

(2S,5R)-1-Boc-2,5-dimethylpiperazine hydrochloride

Similarity: 0.88

Chemical Structure| 313657-42-0

[ 313657-42-0 ]

1-Boc-3-Methylpiperazine hydrochloride

Similarity: 0.88

Chemical Structure| 1188263-76-4

[ 1188263-76-4 ]

tert-Butyl 2-methylpiperazine-1-carboxylate hydrochloride

Similarity: 0.88

Chemical Structure| 1000853-53-1

[ 1000853-53-1 ]

(R)-tert-Butyl 2-methylpiperazine-1-carboxylate hydrochloride

Similarity: 0.88

Chemical Structure| 1384840-46-3

[ 1384840-46-3 ]

(R)-tert-Butyl 3-methylpiperazine-1-carboxylate hydrochloride

Similarity: 0.88