Potassium Carbonate → HCID 57597577, compound

HRID 1786542Notes

Reaction equation

HRID 1786542 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.[CH:15]([NH:28][C:29](=[O:37])[N:30]([CH3:36])[CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[CH:15]([NH:28][C:29](=[O:37])[N:30]([C@@H:31]1[CH2:35][CH2:34][N:33]([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:32]1)[CH3:36])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 69052885HCID 69052885, compound

Product 1

HCID 57597577HCID 57597577, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of bromodiphenylmethane (0.43 g, 1.75 mmol) in butanone (10 ml) was added 3-benzhydryl-1-methyl-1-pyrrolidin-3-yl-urea(0.65 g, 2.1 mmol), K2CO3 (0.24, 1.75 mmol) and KI (0.29 g, 1.75 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 (1:1) gives 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-64ad327fd7e5418c8db679f5c0b209c6
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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