Potassium Carbonate → HCID 89962114, compound

HRID 1496705Notes

Reaction equation

HRID 1496705 reaction equation
Cl.[CH3:2][C:3]1([OH:8])[CH2:7][CH2:6][NH:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[C:15]1([CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[C:15]1([CH:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:5]2[CH2:6][CH2:7][C:3]([CH3:2])([OH:8])[CH2:4]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 533465593-Methylpyrrolidin-3-ol hydrochloride

Product 1

HCID 89962114HCID 89962114, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a reaction flask were added 3-methylpyrrolidin-3-ol hydrochloride (1 g, 7.2 mmol), anhydrous potassium carbonate (2.5 g, 18 mmol) and acetonitrile (50 L). To the resulting mixture was slowly added a solution of diphenylbromomethane (1.78 g, 7.2 mmol) in acetonitrile dropwisely at 85° C. The reaction was conducted for 12 hours. After the completion of reaction monitored by TLC, the resulting mixture was evaporated under reduced pressure to remove acetonitrile. To the residue was added a mixed solution of dichloromethane and water for extraction. The organic phase was dried over anhydrous sodium sulfate and evaporated to remove the solvent to produce a crude product. The crude product was purified by column chromatography (silica gel column, eluted with petroleum ether:ethyl acetate=30:1 (volumetric ratio)) to produce 1-(diphenylmethyl)-3-methylpyrrolidin-3-ol (1 g) in a yield of 52.0%.

Workup

  1. customAfter the completion of reaction
  2. customthe resulting mixture was evaporated under reduced pressure
  3. customto remove acetonitrile
  4. additionTo the residue was added a mixed solution of dichloromethane and water
  5. extractionfor extraction
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. customevaporated
  8. customto remove the solvent
  9. customto produce a crude product
  10. customThe crude product was purified by column chromatography (silica gel column, eluted with petroleum ether:ethyl acetate=30:1 (volumetric ratio))

Sources & evidence

ORD record
ord-35b170d6e4d648ffacc0e6cb0bc799ee
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Reaction notes

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