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[ CAS No. 95635-55-5 ]

{[proInfo.proName]} (Synonyms:CVT 33; RS-43285-3) ,{[proInfo.pro_purity]}
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Chemical Structure| 95635-55-5
Chemical Structure| 95635-55-5
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CAS No. :95635-55-5 MDL No. :MFCD00864690
Formula : C24H33N3O4 Boiling Point : 624.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :427.54 g/mol Pubchem ID :56959
Synonyms :

1. Ranolazine

Safety of [ 95635-55-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 95635-55-5 ]

  • Upstream synthesis route of [ 95635-55-5 ]
  • Downstream synthetic route of [ 95635-55-5 ]

[ 95635-55-5 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 162712-35-8 ]
  • [ 1131-01-7 ]
  • [ 95635-55-5 ]
YieldReaction ConditionsOperation in experiment
34% With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 30 - 35℃; for 18 h; N-(2,6-Dimethyl-phenyl)-2-{4-[2-hydroxy-3-(2-methoxy-phenoxy)-propyl]-piperazin-1-yl}-acetamide:
A mixture of 1-(2-methoxy-phenoxy)-3-piperazin-1-yl-propan-2-ol (2 g, 7.52 mmol), 2-chloro-N-(2,6-dimethyl-phenyl)-acetamide (1.84 g, 9.34 mmol), anhydrous potassium carbonate (2 g, 14.5 mmol) and sodium iodide (74 mg, 0.5 mmol) in dimethylformamide (5 mL) was maintained at 30-35° C. for about 18 hours.
The mixture was quenched with water and standard extractive work up afforded a crude residue which was purified by flash column chromatography on silica gel (2*16 cm, dichloromethane/methanol/triethylamine=100/2/1 elution) to afford the title compound (1.1 g, 34percent).
1H NMR (300 MHz, CDCl3) δ 7.11 (s, 3H), 6.98-6.90 (m, 4H), 4.19 (br. s, 1H), 4.05 (d, 2H, J=5.4 Hz), 3.87 (s, 3H), 3.30-3.24 (m, 2H), 2.76-2.63 (m, 10H), 2.25 (s, 6H); LC-MS: m/z=428 (MH)+; HPLC: 99percent (Purity).
Reference: [1] Patent: US2008/312247, 2008, A1, . Location in patent: Page/Page column 31-32
[2] Patent: WO2006/8753, 2006, A1, . Location in patent: Page/Page column 7; 8
[3] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
  • 2
  • [ 5294-61-1 ]
  • [ 95635-55-5 ]
YieldReaction ConditionsOperation in experiment
87.4% With potassium carbonate In ethanol; toluene for 3 h; Reflux 3.4: 1-bromo-3-(2-methoxyphenoxy)-2-propylalcohol as a raw material[0047][0048]2.6 g (0.014 mol) of 1-bromo-3-(2-methoxyphenoxy)-2-propylalcohol, 3.1 g (0.012 mol) of N-(2,6-dimethylphenyl)-1-piperazinylacetamide, 5.5 g (0.04 mol) of potassium carbonate, 25 ml of ethanol and 50 ml of toluene were successively added into a reaction flask and heated under reflux for 3 h till completion.[0049]The former fraction whose main ingredient was ethanol was collected by atmospheric distillation and then filtrated. The filtrate was washed with 3N HCl to get liquid having a pH of 1-2 and further treated with 50 ml of saturated sodium carbonate solution to adjust pH to 9-10. The product was extracted three times with 25 ml of dichloromethane each and the lower organic phase was combined. After the dichloromethane was removed by distillation under reduced pressure and rotary evaporation, the yellow viscous liquid was obtained and then further dissolved in about 10 ml of methonal. The tetrahydrofuran was then dropwise added under reflux till turbidity. The product was slowly crystallized with cooling and filtrated to get 3.73 g of white solid having a yield of 87.4percent by vacuum drying at 40° C.[0050]The result of 1HNMR (CDCl3) confirmed that the compound obtained is ranolazine. Purity by HPLC (area normalization method): 99.3percent.
Reference: [1] Patent: US2013/90475, 2013, A1, . Location in patent: Paragraph 0047; 0048; 0049; 0050
  • 3
  • [ 25772-81-0 ]
  • [ 5294-61-1 ]
  • [ 95635-55-5 ]
YieldReaction ConditionsOperation in experiment
80.1% With potassium carbonate In methanol; toluene for 4.5 h; Reflux 3.1: 1-chloro-3-(2-methoxyphenoxy)-2-propylalcohol as a raw material[0035][0036]2.5 g (0.01 mol) of 1-chloro-3-(2-methoxyphenoxy)-2-propylalcohol, 3.1 g (0.012 mol) of N-(2,6-dimethylphenyl)-1-piperazinylacetamide, 4.1 g (0.03 mol) of potassium carbonate, 25 ml of methanol and 50 ml of toluene were successively added into a reaction flask and heated under reflux for 4.5 h till completion.[0037]The fraction whose main ingredient was methanol was collected by atmospheric distillation at boiling point of 62-68° C. and then filtrated. The filtrate was washed with 3N HCl to get 50 ml of liquid having a pH of 1-2 and further treated with 50 ml of saturated sodium carbonate solution to adjust pH to 9-10. The product was extracted three times with 20 ml of dichloromethane each and the lower organic phase was combined. After the dichloromethane was removed by distillation under reduced pressure and rotary evaporation, the yellow viscous liquid was obtained and then further dissolved in about 10 ml of methonal. The tetrahydrofuran was then dropwise added under reflux till turbidity. The product was slowly crystallized with cooling and filtrated to get 3.42 g of white solid having a yield of 80.1percent by vacuum drying at 40° C.[0038]1HNMR (CDCl3): 2.22,s, 6H, 2.60˜2.62,t, 4H, 2.75,s, 6H, 3.21,s, 2H, 3.45,s, 3H; 3.85,s, 3H, 4.02˜4.04,t, 2H, 4.16,s, 1H, 6.88˜6.90,t, 2H, 6.91˜6.96,m, 2H, 7.08˜7.1,m, 3H, 8.65,s, 1H. The result confirmed that the compound obtained is ranolazine. Purity by HPLC (area normalization method): 99.1percent.
Reference: [1] Patent: US2013/90475, 2013, A1, . Location in patent: Paragraph 0035; 0036; 0037; 0038
  • 4
  • [ 2210-74-4 ]
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  • [ 95635-55-5 ]
YieldReaction ConditionsOperation in experiment
85% at 70℃; for 2 h; Green chemistry General procedure: Sulfated tungstate (10 wtpercent) was added to a solution of cyclohexene oxide (1 g, 10.18 mmol) and aniline (0.95 g, 10.18 mmol) in solvent-free condition and the mixture was stirred at room temperature. The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate (15 ml) and filtered to recover the catalyst. Organic layer washed with water (10 ml), dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by chromatography on silica gel (60–120) with hexane-ethyl acetate (8:2) as eluent to get pure 2-(phenylamino) cyclohexanol as a white solid.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 48, p. 6455 - 6459
[2] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 11, p. 1218 - 1222
[3] Organic Process Research and Development, 2012, vol. 16, # 5, p. 748 - 754
[4] Patent: WO2008/47388, 2008, A2, . Location in patent: Page/Page column 13; 15
[5] Patent: US2009/318697, 2009, A1, . Location in patent: Page/Page column 4
[6] Patent: WO2010/25370, 2010, A2, . Location in patent: Page/Page column 52
[7] Patent: WO2010/43976, 2010, A2, . Location in patent: Page/Page column 19
[8] Patent: WO2010/97805, 2010, A1, . Location in patent: Page/Page column 9
[9] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
  • 5
  • [ 1427177-23-8 ]
  • [ 90-05-1 ]
  • [ 95635-55-5 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[2] RSC Advances, 2016, vol. 6, # 54, p. 49150 - 49157
  • 6
  • [ 110-85-0 ]
  • [ 2210-74-4 ]
  • [ 1131-01-7 ]
  • [ 95635-55-5 ]
Reference: [1] Patent: WO2016/142819, 2016, A2, . Location in patent: Page/Page column 18; 19
  • 7
  • [ 87-62-7 ]
  • [ 95635-55-5 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 5, p. 748 - 754
[2] Organic Process Research and Development, 2012, vol. 16, # 5, p. 748 - 754
[3] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[4] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[5] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[6] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[7] Patent: US2013/90475, 2013, A1,
[8] Patent: US2013/90475, 2013, A1,
[9] RSC Advances, 2016, vol. 6, # 54, p. 49150 - 49157
[10] Patent: WO2016/142819, 2016, A2,
[11] Patent: WO2016/142819, 2016, A2,
  • 8
  • [ 1131-01-7 ]
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Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 5, p. 748 - 754
[2] Organic Process Research and Development, 2012, vol. 16, # 5, p. 748 - 754
[3] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[4] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[5] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[6] Patent: US2013/90475, 2013, A1,
[7] RSC Advances, 2016, vol. 6, # 54, p. 49150 - 49157
  • 9
  • [ 2210-74-4 ]
  • [ 1131-01-7 ]
  • [ 95635-55-5 ]
Reference: [1] Patent: WO2010/23687, 2010, A2, . Location in patent: Page/Page column 17
  • 10
  • [ 2210-74-4 ]
  • [ 1131-01-7 ]
  • [ 95635-55-5 ]
Reference: [1] Patent: WO2016/142819, 2016, A2, . Location in patent: Page/Page column 19-20
  • 11
  • [ 90-05-1 ]
  • [ 95635-55-5 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 5, p. 748 - 754
[2] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[3] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[4] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[5] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[6] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[7] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[8] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[9] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[10] Patent: US2013/90475, 2013, A1,
[11] Patent: US2013/90475, 2013, A1,
[12] Patent: WO2016/142819, 2016, A2,
  • 12
  • [ 5294-61-1 ]
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Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2005, vol. 61, # 4, p. 665 - 671
[2] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[3] RSC Advances, 2016, vol. 6, # 54, p. 49150 - 49157
  • 13
  • [ 2210-74-4 ]
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Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
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[ 95635-55-5 ]

Chemical Structure| 95635-56-6

A730331[ 95635-56-6 ]

N-(2,6-Dimethylphenyl)-2-(4-(2-hydroxy-3-(2-methoxyphenoxy)propyl)piperazin-1-yl)acetamide dihydrochloride

Reason: Free-salt