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Chemical Structure| 159275-17-9 Chemical Structure| 159275-17-9

Structure of 159275-17-9

Chemical Structure| 159275-17-9

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Product Details of [ 159275-17-9 ]

CAS No. :159275-17-9
Formula : C14H18BrNO2
M.W : 312.20
SMILES Code : O=C(N1CCC(CBr)CC1)OCC2=CC=CC=C2
MDL No. :MFCD02681989
InChI Key :XJHKDSZGAWXUTB-UHFFFAOYSA-N
Pubchem ID :2776274

Safety of [ 159275-17-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P310+P330+P331-P303+P361+P353+P310-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501
Class:8
UN#:1759
Packing Group:

Application In Synthesis of [ 159275-17-9 ]

* 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 [ 159275-17-9 ]

[ 159275-17-9 ] Synthesis Path-Downstream   1~40

  • 1
  • [ 89004-82-0 ]
  • [ 159275-17-9 ]
  • [ 566905-91-7 ]
  • 2
  • [ 122860-33-7 ]
  • [ 159275-17-9 ]
YieldReaction ConditionsOperation in experiment
10 g With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 3h;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.
  • 5
  • [ 10314-98-4 ]
  • [ 159275-17-9 ]
  • 6
  • [ 159275-17-9 ]
  • 7-(1-acetylpiperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinolin-2-carboxamidine [ No CAS ]
  • 7
  • [ 159275-17-9 ]
  • 3-[4-(1,2,3,4-tetrahydro-isoquinolin-7-yloxymethyl)-3,4,5,6-tetrahydro-2<i>H</i>-[1,4']bipyridinyl-3'-yl]-acrylic acid ethyl ester [ No CAS ]
  • 8
  • [ 159275-17-9 ]
  • 7-[1-(2-nitrophenylmethyl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinolin-2-carboxamidine [ No CAS ]
  • 9
  • [ 159275-17-9 ]
  • 7-[1-(3-nitro-benzyl)-piperidin-4-ylmethoxy]-3,4-dihydro-1<i>H</i>-isoquinoline-2-carboxamidine [ No CAS ]
  • 10
  • [ 159275-17-9 ]
  • [ 247133-01-3 ]
  • 11
  • [ 159275-17-9 ]
  • [ 247132-89-4 ]
  • 12
  • [ 159275-17-9 ]
  • [ 247134-34-5 ]
  • 13
  • [ 159275-17-9 ]
  • 7-[1-(3-amino-benzyl)-piperidin-4-ylmethoxy]-3,4-dihydro-1<i>H</i>-isoquinoline-2-carboxamidine; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]
  • 14
  • [ 159275-17-9 ]
  • 7-(piperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinolin-2-carboxamidine [ No CAS ]
  • 15
  • [ 159275-17-9 ]
  • [ 247132-99-6 ]
  • 16
  • [ 159275-17-9 ]
  • [ 247133-05-7 ]
  • 17
  • [ 159275-17-9 ]
  • 7-(1-acetoimidoylpiperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinolin-2-carboxamidine [ No CAS ]
  • 18
  • [ 159275-17-9 ]
  • 7-[1-(pyridin-4-ylmethy)piperidin-4-ylmethoxyl]-1,2,3,4-tetrahydroisoquinolin-2-carboxamidine [ No CAS ]
  • 19
  • [ 159275-17-9 ]
  • 7-[1-(pyridin-2-ylmethy)piperidin-4-ylmethoxyl]-1,2,3,4-tetrahydroisoquinolin-2-carboxamidine [ No CAS ]
  • 20
  • [ 159275-17-9 ]
  • [ 247133-00-2 ]
  • 21
  • [ 159275-17-9 ]
  • 4-[4-(1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-carboxylic acid [ No CAS ]
  • 22
  • [ 159275-17-9 ]
  • [ 247134-35-6 ]
  • 23
  • [ 159275-17-9 ]
  • [ 247133-04-6 ]
  • 24
  • [ 159275-17-9 ]
  • [ 247132-79-2 ]
  • 25
  • [ 159275-17-9 ]
  • 3-[4-[4-(2-amidino-1,2,3,4-tetrahydroisoquinolin-7-ylmethoxy)piperidin-1-yl]piperidin-3-yl]-2-propionic acid [ No CAS ]
  • 26
  • [ 159275-17-9 ]
  • [ 247134-84-5 ]
  • 27
  • [ 159275-17-9 ]
  • [ 247132-92-9 ]
  • 28
  • [ 159275-17-9 ]
  • [ 247132-82-7 ]
  • 29
  • [ 159275-17-9 ]
  • {<i>tert</i>-butoxycarbonylimino-[7-(1-pyridin-2-ylmethyl-piperidin-4-ylmethoxy)-3,4-dihydro-1<i>H</i>-isoquinolin-2-yl]-methyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 30
  • [ 159275-17-9 ]
  • (<i>tert</i>-butoxycarbonylimino-{7-[1-(3-nitro-benzyl)-piperidin-4-ylmethoxy]-3,4-dihydro-1<i>H</i>-isoquinolin-2-yl}-methyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 31
  • [ 159275-17-9 ]
  • [ 854261-83-9 ]
  • 32
  • [ 159275-17-9 ]
  • [ 566905-95-1 ]
  • 33
  • [ 159275-17-9 ]
  • [ 566905-99-5 ]
  • 34
  • [ 159275-17-9 ]
  • 2-[4-(aminomethyl)piperidin-1-yl]ethyl 4-amino-5-chloro-2-methoxybenzoate dihydrochloride [ No CAS ]
  • 35
  • [ 159275-17-9 ]
  • 4-amino-5-chloro-2-methoxy-benzoic acid 2-{4-[(5-dimethylamino-naphthalene-1-sulfonylamino)-methyl]-piperidin-1-yl}-ethyl ester [ No CAS ]
  • 36
  • [ 558-13-4 ]
  • [ 122860-33-7 ]
  • [ 159275-17-9 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; In dichloromethane; Step 3 4-Bromomethylpiperidine-1-carboxylic Acid Benzyl Ester To a solution of 4-hydroxymethylpiperidine-1-carboxylic acid benzyl ester (1.11 g), carbon tetrabromide (1.77 g) in methylene chloride (11 ml) was added triphenylphosphine (1.4 g) with ice-cooling, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:acetone=10:1) and dried under reduced pressure to give the title compound (1.25 g). 1H-NMR (delta ppm, CDCl3) 1.05-1.30 (m, 2H), 1.70-1.90 (m, 3H), 2.78 (m, 2H), 3.29 (d, 2H), 4.10-4.30 (m, 2H), 5.13 (s, 2H), 7.26-7.38 (m, 5H).
  • 37
  • [ 247132-77-0 ]
  • [ 159275-17-9 ]
  • [ 247132-78-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; dimethyl sulfoxide; Step 4 4-[2-(N,N'-Di-tert-Butoxycarbonylamidino)-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl]piperidine-1-carboxylic Acid Benzyl Ester To a solution of N,N'-di-tert-butoxycarbonyl-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine (50 mg) and <strong>[159275-17-9]4-bromomethylpiperidine-1-carboxylic acid benzyl ester</strong> (120 mg) in dimethyl sulfoxide (1 ml) was added 4N aqueous sodium hydroxide solution (0.13 ml), and the mixture was stirred at room temperature for 17 hours. After completion of the reaction, water was added, and the mixture was extracted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:acetone=5:1) and dried under reduced pressure to give the title compound (55 mg). 1H-NMR (delta ppm, CDCl3) 1.20-1.35 (m, 2H), 1.51 (s, 18H), 1.75-2.05 (m, 3H), 2.70-2.95 (m, 4H), 3.65-3.80 (m, 4H), 4.15-4.35 (m, 2H), 4.67 (brs, 2H), 5.14 (s, 2H), 6.61 (1H), 6.71 (1H), 7.03 (1H), 7.30-7.40 (5H).
  • 38
  • [ 159275-16-8 ]
  • [ 159275-17-9 ]
YieldReaction ConditionsOperation in experiment
With lithium bromide; In tetrahydrofuran; water; ethyl acetate; (c) N-Benzyloxycarbonyl-4-bromomethylpiperidine STR78 A mixture comprising 6.6 g of the N-benzyloxycarbonyl-4-(methanesulfonyloxymethyl)piperidine, 5.2 g of lithium bromide and 70 ml of tetrahydrofuran was refluxed for 2 hours to conduct a reaction. After the completion of the reaction, water was added to the reaction mixture. The resulting mixture was extracted with ethyl acetate. The organic phase was dried and distilled to remove the solvent. The residue was purified by silica gel column chromatography ?hexane/ ethyl acetate[(3:1)] to give 5.4 g of the title compound as a colorless oil. 1H-NMR delta(CDCl3): 1.14~1.30(2H, m), 1.75~1.90(3H, m), 2.68~2.85(2H, m), 3.30(2H, d, J=8 Hz), 4.22(2H, s), 5.13(2H, s), 7.18~7.28(5H, m)
  • 39
  • [ 1660-94-2 ]
  • [ 159275-17-9 ]
  • [ 159275-18-0 ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; acetone; (d) Tetraethyl 2-(N-benzyloxycarbonyl-4-piperidinyl)ethylidene-1,1-diphosphonate STR79 3.2 g of the N-benzyloxycarbonyl-4-bromomethylpiperidine prepared in the step (c) was dropwise added to a solution of 3.2 g of tetraethyl methylenediphosphonate and 0.46 g of sodium hydride (60% oil dispersion) in 20 ml of anhydrous dimethylformamide at room temperature. The obtained mixture was stirred at 60 C. for 3 fours and poured into chilled water. The resulting mixture was extracted with ethyl acetate. The organic phase was dried and distilled to remove the solvent. The residue was purified by silica gel column chromatography ?benzene/acetone[(75:25)] to give 2.5 g of the title compound as a colorless oil. 1 H-NMR delta(CDCl3): 1.00~1.15(2H, m), 1.33(12H, t, J=7 Hz), 1.68~1.90(5H, m), 2.47(1H, tt, J=24 Hz, 7 Hz), 2.76(2H, s), 4.10~4.22(10H, m), 5.11(2H, s), 7.28~7.36(5H, m)
  • 40
  • [ 159275-17-9 ]
  • C24H31N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
b) Synthesis of piperidin-4-ylmethyl-pyridin-2-yl-carbamic acid tert-butyl ester (2)); <n="122"/>50 g 2-Aminopyridine (0.53 mol) was stirred with 127 g di-tert-butyl-dicarbonate (0.58 mol) in /er/-butanol at 60 0C over night. The solvent was removed and the crude product was crystallized from toluene to give pyridin-2-yl-carbamic acid ter/-butyl ester.To a solution of 1.3 g (6.4 mmol) pyridin-2-yl-carbamic acid tert-butyl ester in dry DMF 16.6 ml (8.4 mmol) KHMDS (0.5 M in toluene) were added at 0 0C. After complete addition 2.0 g (6.4 mmol) 4-bromomethylpiperidine-l-carboxylic acid benzyl ester were added and the reaction mixture was allowed to come to room temperature over night. 300 ml ethyl acetate were added and the mixture was washed 3 times with 2 N NaOH/brine (2:1) and once with brine. The organic phase was dried over sodium sulfate followed by evaporation under reduced pressure. Chromatography on silica gel with n-hexane/ethyl acetate afforded a Cbz-protected intermediate which was dissolved together with 10% palladium on carbon in methanol and stirred under an atmosphere of hydrogen for 4 h. Removal of the catalyst by filtration through a pad of Celite followed by evaporation of the solvent under reduced pressure yields the desired amine (2).
 

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Technical Information

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