Potassium Carbonate → HCID 68870373, compound

HRID 2111995Notes

Reaction equation

HRID 2111995 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11](=[O:21])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[CH3:22][O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11](=[O:21])[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:24]([O:23][CH3:22])=[O:33])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 68869800HCID 68869800, compound

Product 1

HCID 68870373HCID 68870373, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[3-(3,4-dihydroisoquinolin-2(1H)-yl)-3-oxopropyl]phenol (155 mg, 0.551 mmol) was dissolved in acetonitrile (10 ml). 2-Bromomethylbenzoic acid methyl ester (126 mg, 0.551 mmol) was added followed by potassium carbonate anhydrous (114 mg, 0.826 mmol). The mixture was heated to reflux overnight and then evaporated to dry. Water and ethyl acetate were added and two phases were separated. The organic phase was dried (magnesium sulphate) and evaporated. Column chromatography of the residue on silica gel using ethyl acetate/heptane (40:60) as eluant gave 135 mg the desired product, yield 57%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated
  4. customto dry
  5. additionWater and ethyl acetate were added
  6. customtwo phases were separated
  7. dry with materialThe organic phase was dried (magnesium sulphate)
  8. customevaporated

Sources & evidence

ORD record
ord-f1f39f6824e04b649d7cd1eab7ac1b32
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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