Sodium Iodide → 1-(4-Chlorobenzyl)-6-(dimethylamino)-4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one

HRID 1477693Notes

Reaction equation

HRID 1477693 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[CH:18][NH:17][C:16](=[O:20])[N:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:38][N:39](C)[CH:40]=O>>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:17]2[C:18]([N:39]([CH3:40])[CH3:38])=[N:19][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:13][CH2:12]3)=[N:15][C:16]2=[O:20])=[CH:24][CH:23]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 178517893HCID 178517893, compound

Product 1

HCID 1178401591-(4-Chlorobenzyl)-6-(dimethylamino)-4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-oneYield 1%

Procedure

To an N,N-dimethylformamide solution (5 mL) of 4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one (100 mg, 0.36 mmol) synthesized in Reference Synthesis Example 3, 4-chlorobenzyl chloride (69 mg, 0.43 mmol), potassium carbonate (59 mg, 0.43 mmol), and sodium iodide (54 mg, 0.36 mmol) were added and the resultant mixture was stirred at 90° C. for 5 hours. The reaction solution was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain the title compound (1 mg, yield: 1%).

Workup

  1. additionwere added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ce9b40c17bc04a9fa5fdfecbcb968d46
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

Loading…