Potassium Carbonate → HCID 89961856, compound

HRID 1496699Notes

Reaction equation

HRID 1496699 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+].Br[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH3:2][C:3]1([OH:8])[CH2:7][CH2:6][N:5]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 533465593-Methylpyrrolidin-3-ol hydrochloride2×

Product 1

HCID 89961856HCID 89961856, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

According to Example 15, 3-methylpyrrolidin-3-ol hydrochloride was synthesized. To a 100 mL reaction flask were added 3-methylpyrrolidin-3-ol hydrochloride (1 g, 7.2 mmol), anhydrous potassium carbonate (2.5 g, 18 mmol) and acetonitrile (15 mL). To the resulting mixture was slowly added a solution of 3-bromopropylbenzene (1.29 g, 6.48 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=10:1 (volumetric ratio)) to produce 3-methyl-1-(3-phenylpropyl)pyrrolidin-3-ol (1 g) in a yield of 70.4%.

Workup

  1. customwas synthesized
  2. customTo a 100 mL reaction flask
  3. customAfter the completion of reaction
  4. customthe resulting mixture was evaporated under reduced pressure
  5. customto remove acetonitrile
  6. additionTo the residue was added a mixed solution of dichloromethane and water
  7. extractionfor extraction
  8. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  9. customevaporated
  10. customto remove the solvent
  11. customto produce a crude product
  12. customThe crude product was purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=10:1 (volumetric ratio))

Sources & evidence

ORD record
ord-62432ce9a93a44edb81004c13b8c3659
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Reaction notes

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