Water → HCID 22660605, compound

HRID 392755Notes

Reaction equation

HRID 392755 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)=[O:11].P(Cl)(Cl)(Cl)=O.O.[OH-].[Na+].CN([CH:30]=[O:31])C>>[CH3:18][N:15]1[CH2:14][CH2:13][N:12]([C:10]([C:2]2[NH:1][C:9]3[C:4]([C:3]=2[CH:30]=[O:31])=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:11])[CH2:17][CH2:16]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 4060730(1H-indol-2-yl)(4-methylpiperazin-1-yl)methanone

Product 1

HCID 22660605HCID 22660605, compound

Procedure

(1H-Indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 4, 0.206 g) in DMF (1.5 mL) at 0° C. was treated with phosphorus oxychloride (0.1 mL) over 10 min. The reaction mixture was warmed to ambient temperature and stirred for 16 h. The reaction mixture was poured into water and adjusted to neutral pH by addition of 1 M sodium hydroxide. The mixture was extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated to give crude product. Purification via silica gel chromatography, eluting with 1-8% methanol/dichloromethane afforded the title compound (0.108 g).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product
  6. customPurification via silica gel chromatography
  7. washeluting with 1-8% methanol/dichloromethane

Sources & evidence

ORD record
ord-746e46762c1d4fe0945dee91af9ccd32
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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