Benzyl Bromide → HCID 25030477, compound

HRID 1864444Notes

Reaction equation

HRID 1864444 reaction equation
[C:1]1([S:7]([N:10]2[CH2:14][C@@H:13]([C:15]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=4[CH3:30])[CH2:19][CH2:18]3)=[O:16])[NH:12][C:11]2=[O:31])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.C(OCC)(=O)C>[C:1]1([S:7]([N:10]2[CH2:14][C@@H:13]([C:15]([N:17]3[CH2:18][CH2:19][N:20]([C:23]4[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=4[CH3:30])[CH2:21][CH2:22]3)=[O:16])[N:12]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:11]2=[O:31])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 7498Benzyl Bromide2×HCID 10340Sodium CarbonateHCID 11430Potassium Carbonate2×HCID 67141101HCID 67141101, compound

Product 1

HCID 25030477HCID 25030477, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-1-benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one (40 mg) in acetone (5 mL) was treated with benzyl bromide (0.02 mL) and potassium carbonate (25 mg). The reaction mixture was stirred at ambient temperature overnight, additional benzyl bromide (0.03 mL) and potassium carbonate (37 mg) were added, and the mixture was heated to 70° C. for 5 h. After cooling to room temperature, ethyl acetate and a diluted aqueous solution of Na2CO3 were added. The phases were separated and the inorganic one was extracted with ethyl acetate. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated. Purification by column chromatography (SiO2, n-heptane/ethyl acetate 3:1 to 1:1) yielded (S)-1-benzenesulfonyl-3-benzyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one (41 mg) as a white solid. MS: 533.3 ([M+H]+)

Workup

  1. temperaturethe mixture was heated to 70° C. for 5 h
  2. temperatureAfter cooling to room temperature
  3. customThe phases were separated
  4. extractionthe inorganic one was extracted with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPurification by column chromatography (SiO2, n-heptane/ethyl acetate 3:1 to 1:1)

Sources & evidence

ORD record
ord-599848161383420d9a344391266a4bcc
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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