Oxalic Acid → HCID 131719594, compound

HRID 864358Notes

Reaction equation

HRID 864358 reaction equation
ClCCC[N:5]1[C:10](=O)[C:9]2[C:12](F)=[CH:13][CH:14]=[CH:15][C:8]=2[Si:7](C)(C)[CH2:6]1.C(N(CC)CC)C.C1(N2CCNCC2)C=CC=CC=1.C(O)(=O)C(O)=O>C1(C)C=CC=CC=1.CC(C)=O.C([O-])(=O)C([O-])=O>[SiH2:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH2:10][NH:5][CH2:6]1

Participants

8

Reactant 4

HCID 971Oxalic AcidHCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 19418907HCID 19418907, compound

Product 1

HCID 131719594HCID 131719594, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1140TolueneSolventHCID 71081OxalateSolvent

Procedure

The procedure is carried out as in Example 11, using 1.15 g of 3-(3-chloropropyl)-1,1-dimethyl-5-fluoro-4-oxo-1,2,3,4-tetrahydro-3,1-benzazasiline, 1.1 cm3 of triethylamine and 1.3 g of 1-phenylpiperazine in 23 cm3 of toluene (23 cc). After purification by flash chromatography on a silica column under a nitrogen stream at moderate pressure (0.5-1.5 bar) with a dichloromethane-methanol mixture (98.5-1.5 by volume) as eluent, 0.3 g of 1,1-dimethyl-5-(4-phenyl-1-piperazinyl)-3- [3-(4-phenyl-1-piperazinyl)-propyl]-4-oxo-1,2,3,4-tetrahydro-3,1-benzazasiline; melting point =166° C., and 0.3 g of an oil are obtained, which oil, when dissolved in 3 cm3 of acetone and treated with 0.24 g of oxalic acid, yield 1,1-dimethyl-5-fluoro-4-oxo-3-3-(4-phenyl-1-piperazinyl) 3-propyl]-1,2,3,4,-tetrahydro-3,1-benzazasiline in the oxalate form; melting point =99° C.

Workup

  1. customAfter purification by flash chromatography on a silica column under a nitrogen stream at moderate pressure (0.5-1.5 bar) with a dichloromethane-methanol mixture (98.5-1.5 by volume) as eluent
  2. custompoint =166° C., and 0.3 g of an oil
  3. customare obtained

Sources & evidence

ORD record
ord-b535f79d1c994a48addcbcb12372df1b
Source dataset
uspto-grants-1996_10
Patent number
US05563144

Reaction notes

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