Tetrahydrofuran → HCID 68691135, compound

HRID 1445464Notes

Reaction equation

HRID 1445464 reaction equation
C1C[O:4][CH2:3]C1.[CH2:6]([N:13]1[C@H:18]([CH3:19])[CH2:17][N:16]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22](F)[CH:21]=2)[C@@H:15]([CH3:29])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CO>[CH2:6]([N:13]1[C@H:18]([CH3:19])[CH2:17][N:16]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([O:4][CH3:3])[CH:21]=2)[C@@H:15]([CH3:29])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 68690920HCID 68690920, compound

Product 1

HCID 68691135HCID 68691135, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into 20 ml of THF and 6 ml of methanol was dissolved 5.17 g of 4-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-2-fluorobenzonitrile, and then 9.83 g of potassium t-butoxide was added thereto, followed by stirring at room temperature overnight. A saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with chloroform. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by evaporation and the resulting residue was purified by silica gel column chromatography to obtain 4.72 g of the title compound from an eluate eluted with hexane-ethyl acetate (80:20, v/v).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by evaporation
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c2872e084e7e4522bd866af1a82e25be
Source dataset
uspto-grants-2010_02
Patent number
US07666873B2

Reaction notes

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