Ammonia → HCID 57164664, compound

HRID 1782743Notes

Reaction equation

HRID 1782743 reaction equation
[CH3:1][N:2]([CH3:16])[C:3](=[O:15])[CH2:4][CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10](F)=[CH:9][CH:8]=1.[C:17]1([CH2:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C.C(OC(C)C)(C)C.N>ClCCl.CO.ClCCl>[CH3:1][N:2]([CH3:16])[C:3](=[O:15])[CH2:4][CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([N:27]2[CH2:28][CH2:29][N:24]([CH2:23][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:25][CH2:26]2)=[CH:9][CH:8]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 7914Diisopropyl EtherHCID 759941-Benzylpiperazine2×HCID 81531DiisopropylethylamineHCID 688576344-Fluoro-N,N-dimethyl-γ-oxobenzenebutanamide

Product 1

HCID 57164664HCID 57164664, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

The mixture of 33.48 g (0.15 Mol) of N,N-dimethyl-4-fluoro-γ-oxobenzenebutanoic acid amide, 29.6 g (0.168 Mol) of 1-(phenyl-methyl)piperazine and 6 ml of DIEA was refluxed for 6 hours. Another 30 g (0.17 Mol) of (phenylmethyl)piperazine was added, and the mixture was refluxed for a further 7 hours. The mixture was taken up in a little dichloromethane, and purified by column chromatography on silica gel, using dichloromethane/methanol/conc. ammonia 99/1/0.5 for elution. The residue obtained from the appropriate fractions was stirred with diisopropylether, the formed crystals were then recrystallised from ethanol. 42.22 g (74% of theory) of colourless crystals were obtained, Rf=0.69 (eluant:dichloromethane/methanol/conc. ammonia 95/5/0.5 v/v/v).

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperaturethe mixture was refluxed for a further 7 hours
  3. custompurified by column chromatography on silica gel
  4. washammonia 99/1/0.5 for elution
  5. customThe residue obtained from the appropriate fractions
  6. customthe formed crystals were then recrystallised from ethanol
  7. custom42.22 g (74% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-b8fc1a4764f84eaca83de04dc57dc356
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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