Potassium Carbonate → HCID 57597572, compound

HRID 1786545Notes

Reaction equation

HRID 1786545 reaction equation
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:15]1([N:21]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:22][C:23]([N:25]([CH3:31])[C@@H:26]2[CH2:30][CH2:29][NH:28][CH2:27]2)=[O:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[CH:2]([N:28]1[CH2:29][CH2:30][C@@H:26]([N:25]([CH3:31])[C:23](=[O:24])[CH2:22][N:21]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:27]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 57597579HCID 57597579, compound

Product 1

HCID 57597572HCID 57597572, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of bromodiphenylmethane (0.3 g, 1.23 mmol) in butanone (10 ml) was added (R)-2-diphenylamino-N-methyl-N-pyrrolidin-3-yl-acetamide (0.46 g, 1.5 mmol), K2CO3 (0.17 g, 1.23 mmol) and KI (0.2 g, 1.23 mmol). The mixture was heated under reflux for 18 hours, then filtered and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2, (50 ml) and washed with water (10 ml). Drying over MgSO4 and removal of solvent under reduced pressure followed by column chromatography using Hex:EtOAc (3:1) gave the desired product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in CH2Cl2, (50 ml)
  6. washwashed with water (10 ml)
  7. dry with materialDrying over MgSO4 and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-85194727a3bc4855a7dda35f5106f763
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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