Potassium Carbonate → HCID 68908958, compound

HRID 881664Notes

Reaction equation

HRID 881664 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:38]=[C:39]([O:41][CH3:42])[CH:40]=1)[CH2:36]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:36][C:35]2[CH:38]=[C:39]([O:41][CH3:42])[CH:40]=[C:33]([O:32][CH3:31])[CH:34]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12744903,5-Dimethoxybenzyl BromideHCID 68906807{3-[3-(2,2-Diphenyl-ethylamino)-propoxy]-phenyl}-acetic acid methyl ester

Product 1

HCID 68908958HCID 68908958, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of {3-[3-(2,2-diphenyl-ethylamino)-propoxy]-phenyl}-acetic acid methyl ester (3) (0.30 g, 0.00074 mol) in DMF (10 mL), was added 3,5-dimethoxy-benzyl bromide (0.23 g, 0.0011 mol) and powdered potassium carbonate (0.96 g, 0.007 mol), the reaction mixture was heated and stirred at 45° C. for 18 hours. After cooling, the reaction mixture was diluted with water (30 mL) and extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (15 mL), dried over Na2SO4, concentrated to an oil, which was purified by flash chromatography (8:2 Hexanes/EtOAc) to give the desired product as oil 0.30 g in 92% yield. 1H NMR (CDCl3) δ 7.20 (m, 9H), 7.11 (t, 2H), 6.83 (d, 1H), 6.64 (s, 1H), 6.62 (d, 1H), 6.26 (s, 3H), 4.18 (t, 1H), 3.67 (s, 3H), 3.63 (s, 6H), 3.61 (s, 2H), 3.56 (s, 2H), 3.54 (t, 2H), 3.08 (d, 2H), 2.60 (t, 2H), 1.79 (t, 2H). 13C NMR (CDCl3) δ 173.3, 161.9, 160.5, 144.9, 143.8, 136.6, 130.8, 129.7, 129.6, 127.6, 122.7, 116.9, 114.5, 107.8, 100.6, 67.1, 61.2, 60.8, 56.6, 53.4, 52.0, 51.2, 42.7, 28.2.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc (3×25 mL)
  4. washThe combined organic extracts were washed with brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to an oil, which
  7. customwas purified by flash chromatography (8:2 Hexanes/EtOAc)

Sources & evidence

ORD record
ord-b77dc15408004eeb942c9e1d660a0cfb
Source dataset
uspto-grants-2015_03
Patent number
US08993628B2

Reaction notes

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