N-methyl-2-pyrrolidone → HCID 11048281, compound

HRID 1420780Notes

Reaction equation

HRID 1420780 reaction equation
CN1C(=O)CCC1.Br[CH2:9][CH2:10][C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:12]#[N:13].[Cl:26][C:27]1[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=1)[CH2:30][O:31][CH:32]1[CH2:36][CH2:35][NH:34][CH2:33]1>C(N(CC)CC)C>[Cl:26][C:27]1[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=1)[CH2:30][O:31][CH:32]1[CH2:36][CH2:35][N:34]([CH2:9][CH2:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12]#[N:13])[CH2:33]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 10998319HCID 10998319, compound

Product 1

HCID 11048281HCID 11048281, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
140 °C

Procedure

To 20 ml of NMP was added 2,54 g of 4-bromo-2,2-diphenylbutyronitrile, 1.79 g of 3-(3-chlorobenzyloxy)pyrrolidine and 1.29 g of triethylamine, and the mixture was stirred for 20 hours at 140° C. The reaction mixture was concentrated under reduced pressure and water was added to the residue, and then extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate) to obtain 1.81 g of the aimed compound as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-02273e4a1a0746f2912a56535164966b
Source dataset
uspto-grants-2000_06
Patent number
US06071950

Reaction notes

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