Dimethylformamide → HCID 53650904, compound

HRID 1420148Notes

Reaction equation

HRID 1420148 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=[O:16])[CH2:13][CH2:14]Br)([O-:3])=[O:2].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C.CN(C=O)C>O>[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=[O:16])[CH2:13][CH2:14][N:27]1[CH2:26][CH2:25][N:24]([C:21]2[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=2)[CH2:29][CH2:28]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 752601-(4-Fluorophenyl)piperazineHCID 81531DiisopropylethylamineHCID 54115575HCID 54115575, compound

Product 1

HCID 53650904HCID 53650904, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.8 gm of N-(2-nitro-4-fluorophenyl)-3-bromo-propionamide, 9.0 gm of 1 -(4-fluoro-phenyl)-piperazine, 6.46 gm of diisopropylethylamine and 150 ml DMF was kept for 48 hours at 150° C. Water (300 ml) was added at ambient temperature and the mixture was extracted with CHCl3. The CHCl3 extract was collected, washed with 20 ml water and dried over Na2SO4. The crude product obtained after removing the solvents was purified by using chromatography: solid phase (SIO2 ; 40 μm; Baker); eluent CHCI3. A sample of this purified material (12.7 gm) exhibited the following data. M+/z of 405.

Workup

  1. extractionthe mixture was extracted with CHCl3
  2. extractionThe CHCl3 extract
  3. customwas collected
  4. washwashed with 20 ml water
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-463cb23c7d60415b92ecaca860032ec2
Source dataset
uspto-grants-1999_03
Patent number
US05889010

Reaction notes

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