Toluene → 3-[(4-chlorophenyl)methyl]-2-cyclopropyl-5,6-dihydrocyclopenta[d]imidazol-4(3H)-one

HRID 1946497Notes

Reaction equation

HRID 1946497 reaction equation
[CH:1]1([C:4]2[NH:8][C:7]3[CH2:9][CH2:10][C:11](=[O:12])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C1(C)C=CC=CC=1.[NH4+].[Cl-]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:5]2[C:6]3[C:11](=[O:12])[CH2:10][CH2:9][C:7]=3[N:8]=[C:4]2[CH:1]2[CH2:3][CH2:2]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 58460160HCID 58460160, compound

Product 1

HCID 584602283-[(4-chlorophenyl)methyl]-2-cyclopropyl-5,6-dihydrocyclopenta[d]imidazol-4(3H)-oneYield 49.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

Tetrabutylammonium bromide (270 mg) was added to a stirred mixture of Intermediate 28 (272 mg), 4-chlorobenzyl bromide (414 mg) in sodium hydroxide 20% aq. (3.09 mL) and toluene (10 mL). The RM was stirred at room temp under nitrogen atm. for 16 hours. Sat. NH4Cl aq. solution (50 mL) was added and the mixture was extracted with EtOAc (2×50 ml). The organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (238 mg). LC/MS MH+ 387, Rt 2.51 min (5 minute run)

Workup

  1. extractionthe mixture was extracted with EtOAc (2×50 ml)
  2. customdried (hydrophobic frit)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on silica using a cyclohexane
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-97a5682e87614d04a0871e33e50e887d
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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