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Potassium Carbonate → Cyclopropyl-(3-ethynyl-phenyl)-methyl-amine

HRID 2377437
Notes
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Reaction equation

HRID 2377437 reaction equation
[CH:1]1([N:4]([CH3:17])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][Si](C)(C)C)[CH:6]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([N:4]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[CH:12])[CH:6]=2)[CH3:17])[CH2:2][CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57424251Cyclopropyl-methyl-(3-trimethylsilanylethynyl-phenyl)-amine2×

Product 1

HCID 21107261Cyclopropyl-(3-ethynyl-phenyl)-methyl-amineYield 102.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of cyclopropyl-methyl-(3-trimethylsilanylethynyl-phenyl)-amine (Intermediate 114, 0.05 g, 0.2 mmol) in methanol (5 mL) was treated with potassium carbonate (0.063 g, 0.46 mmol) and the resulting reaction mixture was heated at 80° C. for 3 h. The solvent was evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound (0.035 g, 100%).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a0e417920327403f99a0bc0fc3efa06d
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07468391B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes