1-(4-Fluorophenyl)piperazine → HCID 59833503, compound

HRID 1402983Notes

Reaction equation

HRID 1402983 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[F:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:35][CH:34]=1.[O:45]=[C:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:49]([CH2:56][C:57]2[CH:58]=[C:59]([CH:63]=[CH:64][CH:65]=2)[C:60](O)=[O:61])=[N:48][NH:47]1>CC(N(C)C)=O.O>[F:32][C:33]1[CH:34]=[CH:35][C:36]([N:39]2[CH2:44][CH2:43][N:42]([C:60]([C:59]3[CH:58]=[C:57]([CH:65]=[CH:64][CH:63]=3)[CH2:56][C:49]3[C:50]4[C:55](=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:46](=[O:45])[NH:47][N:48]=3)=[O:61])[CH2:41][CH2:40]2)=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 752601-(4-Fluorophenyl)piperazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 251319063-((4-Oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid

Product 1

HCID 59833503HCID 59833503, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (150 mg, 0.47 mmol), diisopropylethylamine (102 mg, 0.8 mmol) and 1-(4-fluorophenyl)piperazine (65 mg, 0.47 mmol) were added sequentially at ambient temperature to a stirred solution of 3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)benzoic acid (A)(100 mg, 0.36 mmol) in dry dimethylacetamide (1 ml), the mixture was stirred at ambient temperature for 4 hours and allowed to stand at ambient temperature for 16 hours, then it was added dropwise to stirred cold water (10 ml). After 30 minutes, the resulting solid was collected by filtration, washed with water (2×1 ml) and hexane (1 ml), dried in vacuo and purified using preparative HPLC to give 4-{3-[4-(4-fluorophenyl)piperazin-1-ylcarbonyl]benzyl}-1(2H)-phthalazinone (21)(76 mg) as a cream solid; m/z (M+H)+. 443; HPLC Purity 90%; HPLC Retention time 4.00 minutes.

Workup

  1. waitto stand at ambient temperature for 16 hours
  2. additionit was added dropwise
  3. waitAfter 30 minutes
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with water (2×1 ml) and hexane (1 ml)
  6. customdried in vacuo
  7. custompurified

Sources & evidence

ORD record
ord-596ce2c047374c04ba0f2673518dac07
Source dataset
uspto-grants-2014_12
Patent number
US08912187B2

Reaction notes

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