1-Phenylpiperazine → HCID 13537621, compound

HRID 638561Notes

Reaction equation

HRID 638561 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])[CH:4]=1.[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>CCOCC.CC(C)=O.CCOCC>[C:17]1([N:23]2[CH2:28][CH2:27][N:26]([CH2:2][C:3]3[O:7][N:6]=[C:5]([C:8]([C:10]4[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=4)=[O:9])[CH:4]=3)[CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 70961-PhenylpiperazineHCID 20252673HCID 20252673, compound

Product 1

HCID 13537621HCID 13537621, compoundYield 115.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584533Acetone diethyletherSolvent

Procedure

A solution of 3.7 g of (5-bromomethylisoxazol-3-yl)-4-fluorophenylmethanone in 100 ml of Et2O was added dropwise to a solution of 5.2 g of N-phenylpiperazine in 400 ml of 20% acetone/Et2O. The resulting mixture was stirred at room temperature for 24 hours. This mixture was filtered and the solution was washed with water (2×200 ml) and saturated NaCl, and dried over MgSO4. Concentration of the product gave 5.5 g of a solid which was dissolved in 100 ml of CH2Cl2 and stirred with 5 g of SiO2. This mixture was filtered, the silica washed with CH2Cl2, and the organics were evaporated to give 3.7 g of a solid. The amine was recrystallized from 135 ml of 8% toluene/hexane to yield 2.5 g (53%) of needles, m.p. 94°-95°.

Workup

  1. filtrationThis mixture was filtered
  2. washthe solution was washed with water (2×200 ml) and saturated NaCl
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-4f29ed0a5a6c4a028d9a13ff81ea2ff3
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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