Potassium Carbonate → HCID 89961841, compound

HRID 1496702Notes

Reaction equation

HRID 1496702 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+].[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([F:24])[CH:23]=1)[CH2:19]Br>C(#N)C>[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([F:24])[CH:23]=1)[CH2:19][N:5]1[CH2:6][CH2:7][C:3]([CH3:2])([OH:8])[CH2:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5188963,5-Difluorobenzyl bromideHCID 533465593-Methylpyrrolidin-3-ol hydrochloride2×

Product 1

HCID 89961841HCID 89961841, compound

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 3,5-difluorobenzyl bromide (1.64 g, 7.9 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 of 1-(3,5-difluorobenzyl)-3-methylpyrrolidin-3-ol (1.8 g), which was directly used in the next step.

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

Sources & evidence

ORD record
ord-5f51e6eae93d4f0eaf21bb1fb54a7aa1
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Reaction notes

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