Dichloromethane → HCID 19012036, compound

HRID 1729297Notes

Reaction equation

HRID 1729297 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].ClCCl.[NH2:11][C:12]1[CH:37]=[CH:36][C:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[N:31]([CH3:32])[C:30](=[O:33])[N:29]([CH3:34])[C:28](=[O:35])[CH:27]=3)[CH2:22][CH2:21]2)=[CH:14][CH:13]=1>C(Cl)(Cl)Cl.[OH-].[Na+]>[CH3:32][N:31]1[C:26]([N:23]2[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][CH2:17][O:16][C:15]3[CH:36]=[CH:37][C:12]([NH:11][C:3](=[O:4])[C:2]([F:7])([F:6])[F:1])=[CH:13][CH:14]=3)[CH2:21][CH2:22]2)=[CH:27][C:28](=[O:35])[N:29]([CH3:34])[C:30]1=[O:33]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 10090741HCID 10090741, compound

Product 1

HCID 19012036HCID 19012036, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.5 ml of anhydrous trifluoroacetic acid was added dropwise at 0° C. to 20 ml of a dichloromethane solution containing 1.1 g of 6-[4-(3-[4-aminophenoxy]propyl)piperazin-1-yl]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione obtained in Example 6, and the solution was then stirred at the same temperature for 10 minutes and further at room temperature for 1 hour. Next, the reaction mixture was diluted with 100 ml of chloroform and 50 ml of a 0.5N aqueous sodium hydroxide solution so as to dissolve insolubles therein, and the resultant organic layer was then separated. The aqueous layer was neutralized and then extracted with 50 ml of chloroform, and the extract layer was mixed with the organic layer previously separated and the mixture was dried and then concentrated to obtain 0.52 g (yield: 38% ) of 1,3-dimethyl-6-[4-(3-[4-trifluoroacetylaminophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. dissolutionto dissolve insolubles
  2. customthe resultant organic layer was then separated
  3. extractionextracted with 50 ml of chloroform
  4. additionthe extract layer was mixed with the organic layer
  5. custompreviously separated
  6. customthe mixture was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a593c1b2b0524d10bde1f82b52ad1aa8
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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