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N,N'-Dimethylethylenediamine → 3-(Benzyloxy)-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one

HRID 625945
Notes
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Reaction equation

HRID 625945 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([CH:24]2[CH2:28][NH:27][C:26](=[O:29])[CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>O1CCOCC1.C(Cl)Cl.[Cu]I>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([N:27]2[CH2:28][CH:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:25][C:26]2=[O:29])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 1213974-Phenyl-2-pyrrolidinoneHCID 674178603-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one

Product 1

HCID 674205813-(Benzyloxy)-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-oneYield 103%

Reagents, catalysts & solvents

3
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

3-(Benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one (100 mg, 0.340 mmol), 4-phenylpyrrolidin-2-one (71 mg, 0.440 mmol), K3PO4 (144 mg, 0.680 mmol), CuI (4 mg, 0.021 mmol), and N,N′-dimethylethylenediamine (5 μl, 0.046 mmol) were combined in 1,4-dioxane (1 mL) in a screw cap vial. The vial was sealed then heated to 110° C. After heating overnight the mixture was cooled to RT and diluted with CH2Cl2. The resulting mixture was filtered through a pad of Celite®, washing with CH2Cl2, and concentrated. Flash column (Biotage-SNAP-25 g, 0-10% MeOH/CH2Cl2) gave the title compound (131 mg, 103%) as an off-white foam which was sufficiently pure for use in the next step. 1H NMR (500 MHz, CDCl3): δ 7.44-7.24 (m, 11 H); 7.09 (s, 1 H); 5.15 (s, 2 H); 3.97 (s, 1 H); 3.71-3.65 (m, 2 H); 3.59 (s, 3 H); 3.00-2.92 (m, 1 H); 2.74 (dd, S=16.9, 8.1 Hz, 1 H). LC/MS (M+H)+ 375.

Workup

  1. customcap vial
  2. customThe vial was sealed
  3. temperatureAfter heating overnight the mixture
  4. temperaturewas cooled to RT
  5. filtrationThe resulting mixture was filtered through a pad of Celite®
  6. washwashing with CH2Cl2
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c1ca9904ef964c72ad11272ad4f736ad
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309199B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes