1-Phenylpiperazine → HCID 59850056, compound

HRID 215899Notes

Reaction equation

HRID 215899 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C@H:12]([CH3:16])[C:13]([OH:15])=O)[CH2:7][CH2:6][CH2:5]2.[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C@H:12]([CH3:16])[C:13]([N:26]1[CH2:27][CH2:28][N:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:24][CH2:25]1)=[O:15])[CH2:7][CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57425927HCID 57425927, compound

Product 1

HCID 59850056HCID 59850056, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The (R)-2-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)propanoic acid (7.9 mmol), 1-phenyl piperazine (1.2 mL, 7.9 mmol), HATU (3.0 g, 7.9 mmol), NaHCO3 (660 mg, 7.9 mmol) and CH2Cl2 (10 mL): DMF (10 ml) were stirred at rt for 19 h. The solution was poured into an ice-water mixture (100 ml), followed by an extraction with CH2Cl2 (3×75 mL). The organic layer was dried over MgSO4 and evaporated in vacuo. After evaporating the solvents under reduced pressure, the residue was purified by silica gel chromatography using 20-50% ethyl acetate in hexane gave (R)-2-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)-1-(4-phenylpiperazin-1-yl)propan-1-one (1.96 g) as white solid. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=369.47; tR=3.36 min.

Workup

  1. extractionfollowed by an extraction with CH2Cl2 (3×75 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo
  4. customAfter evaporating the solvents under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8c2f001bbae842d3a07187602a5562b5
Source dataset
uspto-grants-2012_06
Patent number
US08193194B2

Reaction notes

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