3-Phenylpyrrolidine → HCID 25116799, compound

HRID 408666Notes

Reaction equation

HRID 408666 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[CH:10]=2)[N:5]=[C:4]([CH3:18])[CH:3]=1.[C:19]1([CH:25]2[CH2:29][CH2:28][NH:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCCO)C.[OH-].[Na+]>[CH3:18][C:4]1[CH:3]=[C:2]([N:27]2[CH2:28][CH2:29][CH:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26]2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[CH2:16][CH2:15][CH2:14][C:13]3=[O:17])[CH:10]=2)[N:5]=1

Participants

5

Reactant 2

HCID 31467433-PhenylpyrrolidineHCID 68725213HCID 68725213, compound

Product 1

HCID 25116799HCID 25116799, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 8076Glycol monoethyl etherSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of 1-(4-chloro-2-methylquinolin-6-yl)pyrrolidin-2-one (0.2 g; see Preparation 6 above) and 3-phenylpyrrolidine (0.282 g) in 2-ethoxyethanol was heated in a microwave at 250° C. for 20 minutes. The reaction mixture was diluted with 1 N sodium hydroxide and extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. Trituration from ether gave the title compound as a white powder (0.08 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b1d246bf548a4372b8258161aaf8088e
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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