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Product Details of [ 6274-57-3 ]

CAS No. :6274-57-3 MDL No. :MFCD00032473
Formula : C9H12BrN Boiling Point : -
Linear Structure Formula :- InChI Key :RFEDQTSVZVRTGH-UHFFFAOYSA-N
M.W : 214.10 Pubchem ID :235757
Synonyms :

Safety of [ 6274-57-3 ]

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

Application In Synthesis of [ 6274-57-3 ]

* 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 [ 6274-57-3 ]
  • Downstream synthetic route of [ 6274-57-3 ]

[ 6274-57-3 ] Synthesis Path-Upstream   1~13

  • 1
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  • [ 589-15-1 ]
  • [ 6274-57-3 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In tetrahydrofuran; water at 60℃; for 24 h; Inert atmosphere To a flask containing aq dimethylamine (50percent, 500 mmol) and K2CO3 (50 mmol) was added dropwise a solution of 4-bromobenzyl bromide (50 mmol) in THF (90 mL). The obtained mixture was stirred for 24 h at 60 °C under Ar atmosphere. Then, water (60 mL) was added to the reaction mixture and the solution was extracted with CHCl3 (100 mL×3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, 4-bromobenzyldimethylamine was obtained in 99percent yield (bp 55 °C/1 mmHg). Mg (40 mmol) was dried by a vacuum pump for 20 min at 70 °C. To the flask containing Mg was added a solution of 4-bromobenzyldimethylamine (30 mmol) in dry THF (70 mL), and the obtained mixture was stirred for 1 h at room temperature under Ar atmosphere. Then, chlorodiphenylphosphine (30 mmol) in dry THF (30 mL) was added to the mixture at 0 °C and the obtained mixture was stirred for 2 h at room temperature under Ar atmosphere. After the reaction, the mixture was filtered and washed with dichloromethane. Then, aq H2O2 (30percent, 60 mmol) was added to the obtained filtrate at 0 °C and the obtained mixture was stirred for 1 h at room temperature. After the reaction, the reaction mixture was quenched with water (100 mL) and extracted with chloroform (50 mL×3). The organic layer was washed with brine and dried over Na2SO4. After filtration and removal of the solvent, diethyl ether (300 mL) was added to the residue and the mixture was stirred for 0.5 h to dissolve the product. Then, the organic solution was filtered and removal of the solvent from the filtrate gave   4-(diphenylphosphono)benzyldimethylamine in 95percent yield.   Dimethyl sulfate (120 mmol) was added to a flask containing 4-(diphenylphosphono)benzyl-dimethylamine (60 mmol) in dry 1,2-dimethoxyethane (200 mL) at 0 °C. The obtained mixture was stirred for 1 h at 50 °C under Ar atmosphere. Then, LiAlH4 (180 mmol) was added to the solution at 0 °C and the obtained mixture was stirred for 2 h at room temperature. The reaction mixture was quenched with ice and then with aq HBr solution (1 M, 200 mL), and the obtained solution was washed with diethyl ether (200 mL×2). Then, the aqueous solution was extracted with dichloromethane (100 mL×3) and the combined organic layer was dried over Na2SO4. After filtration and removal of the solvent, diethyl ether (300 mL) was added to the residue and the mixture was stirred for 0.5 h under Ar atmosphere. Then, the mixture was filtered to give 4-(diphenylphosphino)benzyltrimethyl-ammonium bromide in 79percent yield.
58% With potassium carbonate In ethanol at 50℃; A solution of l-bromo-4-(bromomethyl)benzene (20 g, 80.65 mmol, 1.00 equiv), dimethylamine (13.20 g, 96.80 mmol, 1.20 equiv, 33percent) and potassium carbonate (13.36 g, 96.81 mmol, 1.20 equiv) in ethanol (200 mL) was stirred overnight at 50°C. The solid material was removed by filtration and the filtrate was concentrated under vacuum. The residue was dissolved in 200 mL of water and extracted with 3x200 mL of dichloromethane. The combined organic layer was washed with 3x200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (20: 1) to give 10 g (58percent) of (4-bromophenyl)-N,N-dimethylmethanamine as a yellow oil. LC-MS: (ES, m/z): 255 [M+CH3CN+H]+, 214 [M+H]+, 169.
58% With potassium carbonate In ethanol at 50℃; A solution of 1-bromo-4-(bromomethyl)benzene (20 g, 80.65 mmol, 1.00 equiv), dimethylamine (13.20 g, 96.80 mmol, 1.20 equiv, 33percent) and potassium carbonate (13.36 g, 96.81 mmol, 1.20 equiv) in ethanol (200 mL) was stirred overnight at 50° C. The solid material was removed by filtration and the filtrate was concentrated under vacuum. The residue was dissolved in 200 mL of water and extracted with 3*200 mL of dichloromethane. The combined organic layer was washed with 3*200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (20:1) to give 10 g (58percent) of (4-bromophenyl)-N,N-dimethylmethanamine as a yellow oil. LC-MS: (ES, m/z): 255 [M+CH3CN+H]+, 214 [M+H]+, 169.
Reference: [1] Tetrahedron, 2010, vol. 66, # 19, p. 3421 - 3426
[2] Tetrahedron, 2013, vol. 69, # 19, p. 3971 - 3977
[3] Chemical Communications, 2012, vol. 48, # 63, p. 7823 - 7825
[4] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8520 - 8529
[5] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2667 - 2677
[6] Journal of the American Chemical Society, 2017, vol. 139, # 28, p. 9519 - 9522
[7] Journal of the American Chemical Society, 1983, vol. 105, # 13, p. 4136 - 4142
[8] Angewandte Chemie - International Edition, 2012, vol. 51, # 48, p. 12000 - 12004[9] Angew. Chem., 2012, vol. 124, # 48, p. 12166 - 12170,4
[10] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1325 - 1330
[11] Patent: WO2013/155338, 2013, A2, . Location in patent: Page/Page column 163
[12] Patent: US2015/329503, 2015, A1, . Location in patent: Paragraph 0685; 0686
[13] Chemistry - A European Journal, 2007, vol. 13, # 33, p. 9372 - 9383
[14] Journal of pharmaceutical sciences, 1962, vol. 51, p. 881 - 884
[15] Archiv der Pharmazie, 1962, vol. 295 /67, p. 690 - 697
[16] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 3993 - 3997
[17] Patent: WO2004/63186, 2004, A1, . Location in patent: Page 26
[18] Patent: WO2009/112565, 2009, A1, . Location in patent: Page/Page column 39
[19] Journal of the American Chemical Society, 2009, vol. 131, # 41, p. 14679 - 14687
[20] Patent: WO2011/60228, 2011, A1, . Location in patent: Page/Page column 63
[21] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 684 - 701
  • 2
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  • [ 6274-57-3 ]
YieldReaction ConditionsOperation in experiment
86% With 1,2-bis(dimethylsilyl)benzene; C22H34FeO2Si4 In toluene at 100℃; for 0.5 h; Inert atmosphere A three-way cock was attached to a 20 mL eggplant flask,After a magnetic stirrer was added and the mixture was heated and dried under reduced pressure to 5 Pa,The inside of the flask was replaced with an argon atmosphere.Iron complex A (1.0 mg, 0.002 mmol) was added as a catalyst to the flask,Was dissolved in toluene (0.5 mL).To this solution was added 1,2-bis (dimethylsilyl) benzene (475 μL) with a syringe,N, N-Dimethyl-4-bromobenzamide (228 mg, 1.0 mmol) was then added.The solution was stirred at 100 & lt; 0 & gt; C for 30 minutes,Toluene was distilled off under reduced pressure.The resulting crude product was purified by column chromatography on silica gel using hexane / ethyl acetate (20/1) as eluent,To obtain 184 mg (0.86 mmol, 86percent) of N, N-dimethyl-4-bromobenzylamine.The results are shown in Table 5 as entry 2. The amine obtained was 1H,13The structure was confirmed by C-NMR spectrum and IR spectrum.
86 %Spectr. at 25℃; for 23 h; Inert atmosphere Three way cock was adhered to the kinds flask of 20mL and after the magnetic stirring bar was added and it reduced pressure to 5Pa it heated and dries inside of the flask was substituted for with the argon atmosphere. Ruthenium complex As (2.4mg, 4.5×10(sup)-3(/sup)mmol) were added to the flask as the catalyst. Here, after the dimethylphenyl silane (681μL) was added through the syringe N,N- dimethyl -4- bromo benzamides (228mg, 1.0mmol) were added. In 25 the solution, the dimethylphenyl silane remaining was removed by distillation after doing 23 hours mixing under the reduced pressure. The obtained crude product was refined to the silica gel filling column chromatography the hexane / ethyl acetate (20/1) to the developing solvent and N,N- dimethyl -4- bromobenzylamine 184 mgs (0.86mmol, 86percent) were obtained
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 50, p. 9511 - 9514
[2] Chemical Communications, 2011, vol. 47, # 23, p. 6581 - 6583
[3] Chemical Communications, 2016, vol. 52, # 82, p. 12195 - 12198
[4] RSC Advances, 2017, vol. 7, # 80, p. 50729 - 50738
[5] Journal of the American Chemical Society, 2009, vol. 131, # 41, p. 15032 - 15040
[6] Dalton Transactions, 2013, vol. 42, # 48, p. 16687 - 16692
[7] Patent: KR2015/125983, 2015, A, . Location in patent: Paragraph 0248-0250
[8] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 79, p. 11192 - 11195
[9] Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13326 - 13329[10] Angew. Chem., 2016, vol. 128, # 42, p. 13520 - 13523,4
[11] Journal of Organic Chemistry, 1982, vol. 47, # 1, p. 34 - 46
[12] Angewandte Chemie - International Edition, 2013, vol. 52, # 44, p. 11577 - 11580[13] Angew. Chem., 2013, vol. 125, # 44, p. 11791 - 11794,4
[14] Patent: KR2015/121721, 2015, A, . Location in patent: Paragraph 0220-0221; 0230
  • 3
  • [ 506-59-2 ]
  • [ 1122-91-4 ]
  • [ 6274-57-3 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 19, p. 5122 - 5125
[2] Journal of Organic Chemistry, 2013, vol. 78, # 8, p. 3688 - 3696
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1320 - 1336
  • 4
  • [ 1122-91-4 ]
  • [ 124-40-3 ]
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Reference: [1] Synthetic Communications, 2000, vol. 30, # 11, p. 2001 - 2008
[2] Science, 2017, vol. 358, # 6361, p. 326 - 332
  • 5
  • [ 1122-91-4 ]
  • [ 124-40-3 ]
  • [ 103-83-3 ]
  • [ 6274-57-3 ]
Reference: [1] Patent: WO2015/32653, 2015, A1, . Location in patent: Page/Page column 34-35
[2] RSC Advances, 2018, vol. 8, # 27, p. 15202 - 15206
  • 6
  • [ 589-15-1 ]
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Reference: [1] Patent: US4496567, 1985, A,
  • 7
  • [ 18469-37-9 ]
  • [ 17985-72-7 ]
  • [ 6274-57-3 ]
Reference: [1] Patent: US2016/23196, 2016, A1,
  • 8
  • [ 21928-11-0 ]
  • [ 17985-72-7 ]
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Reference: [1] Patent: US2016/23196, 2016, A1,
  • 9
  • [ 18469-37-9 ]
  • [ 766-77-8 ]
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Reference: [1] Patent: US2016/23197, 2016, A1,
  • 10
  • [ 3853-06-3 ]
  • [ 589-15-1 ]
  • [ 6274-57-3 ]
  • [ 196394-91-9 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2009, vol. 52, # 1, p. 23 - 28
  • 11
  • [ 106-38-7 ]
  • [ 6274-57-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 684 - 701
  • 12
  • [ 6274-57-3 ]
  • [ 699-03-6 ]
  • [ 1122-91-4 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1985, # 2, p. 64 - 65
[2] Journal of the Chemical Society, Chemical Communications, 1985, # 2, p. 64 - 65
  • 13
  • [ 688-74-4 ]
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Reference: [1] Patent: WO2007/18941, 2007, A2, . Location in patent: Page/Page column 58
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