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Chemical Structure| 57420-88-9 Chemical Structure| 57420-88-9

Structure of 57420-88-9

Chemical Structure| 57420-88-9

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Product Details of [ 57420-88-9 ]

CAS No. :57420-88-9
Formula : C11H17NO
M.W : 179.26
SMILES Code : CC1=C(OCCCN)C(C)=CC=C1
MDL No. :MFCD09739018

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Application In Synthesis of [ 57420-88-9 ]

* 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 [ 57420-88-9 ]

[ 57420-88-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 2314-36-5 ]
  • [ 57420-88-9 ]
  • 2,6-dichloro-4-((3-(2,6-dimethylphenoxy)propylamino)methyl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% General procedure: [0122] A mixture of amine (1 eq.), aldehyde (1.2 eq.) and MeOH (5 mL/mmol amine) was stirred at room temperature under N2 until no more amine was visible by thin-layer chromatography. NaBH4 (1-2 eq.) was added and the mixture was stirred at r.t. for 30-60 min. The mixture was poured into sat. aq. NaHC03 and extracted with Et20 or EtOAc (3 times). The combined organic extracts were dried (MgS04), filtered, and the crude mixture purified according to Protocol A or B (below) to obtain products as their pure hydrochloride salts (see below).[0126] The dried organic extract was concentrated in vacuo and pure free-base was purified by flash chromatography using either EtO Ac/petroleum spirits (10 to 100percent with 1-2percent Et3N) or EtOAc/MeOH/H20/Et3N (97:2: 1:2 to 7:2: 1:0.2). After evaporation of the eluent the remaining Et3N was removed by azeotroping with dichloromethane. The free base was converted to the hydrochloride salt by either dissolving in Et20 and adding 1 M HCl in MeOH or dissolving in MeOH and adding aq. HCl (either 1 M or 10 M). Where necessary compounds were crystallized or recrystallized from MeOH/Et20, MeOH/H20, EtOH/H20, EtOH/THF, MeCN/H20 or MeOH/THF, as noted.Method Al applied to 3-(2,6-dimethylphenoxy)propylamine, followed by purification Protocol B (MeOH/H20) afforded the title compound (318 mg, 64percent). 1H NMR (400 MHz, CD3OD) delta 2.19-2.24 (8 H, m, 2 x CH3,CH2CH2N), 3.33-3.35 (2 H, m, CH2N), 3.87 (2 H, t, J 5.9 Hz, CH20), 4.19 (2 H, s, ArCH2N), 6.89 (1 H, t, J 7.5 Hz, Ar), 6.98-7.00 (2 H, m, Ar), 7.53 (2 H, s, Ar); 13C NMR (100 MHz, CD3OD) delta 16.41, 28.11, 46.36, 50.93, 69.93, 123.82, 123.84, 124.82, 125.25, 129.95, 131.47, 131.68, 151.98, 156.60; [0128] HRMS (ESI+): m/z 354.1027 [M+H]+ (calcd. [Ci8H2iCl2N02+H]+ 354.1022).
  • 2
  • [ 3240-35-5 ]
  • [ 57420-88-9 ]
  • 4-((3-(2,6-dimethylphenoxy)propylamino)methyl)benzenesulfonamide hydrochloride [ No CAS ]
  • 3
  • [ 2314-36-5 ]
  • [ 57420-88-9 ]
  • 2,6-dichloro-4-((3-(2,6-dimethylphenoxy)propylamino)methyl)phenol hydrochloride [ No CAS ]
References: [1]ChemMedChem,2019.
 

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