Formaldehyde → HCID 22660561, compound

HRID 392757Notes

Reaction equation

HRID 392757 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].[CH2:19]=O.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.[OH-].[Na+]>C(O)(=O)C.O>[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[CH2:19][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:11])[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 4060730(1H-indol-2-yl)(4-methylpiperazin-1-yl)methanone

Product 1

HCID 22660561HCID 22660561, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

(1H-Indol-2-yl)-(4-methyl-piperazin-1-yl)-methanone (Example 4, 0.231 g) in acetic acid (1.5 mL) at ambient temperature was treated with paraformaldehyde (0.4 g) and pyrrolidine (0.16 mL). The reaction mixture was heated at 60° for 6 h then poured into water and the solution adjusted to basic 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 (0.1 g).

Workup

  1. temperatureThe reaction mixture was heated at 60° for 6 h
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product
  7. customPurification via silica gel chromatography
  8. washeluting with 1-8% methanol/dichloromethane

Sources & evidence

ORD record
ord-896a3d3d145d4d5299a6567bd95f012a
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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