Formaldehyde → HCID 14254900, compound

HRID 1762422Notes

Reaction equation

HRID 1762422 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][O:9][C:10]([CH:12]1[N:16]([CH2:17][C:18]#[CH:19])[C:15](=[O:20])[CH2:14][CH2:13]1)=[O:11].C=O.N1CCC[C:24]1=O>CO.O1CCOCC1>[CH3:8][O:9][C:10]([CH:12]1[N:16]([CH2:17][C:18]#[C:19][CH2:1][N:2]2[CH2:7][CH2:6][N:5]([CH3:24])[CH2:4][CH2:3]2)[C:15](=[O:20])[CH2:14][CH2:13]1)=[O:11]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 120252-PyrrolidoneHCID 531671-Methylpiperazine2×HCID 14254893HCID 14254893, compound

Product 1

HCID 14254900HCID 14254900, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of N-methylpiperazine (7.0 g), 5-methoxycarbonyl-1-(2-propynyl)-2-pyrrolidinone (12.86 g), paraformaldehyde (2.8 g), cuprous chloride (0.3 g) and anhydrous dioxane (50 ml) was held for 30 min at 58° C. Thin layer chromatographic analysis (silica gel, methanol) indicated the presence of the starting pyrrolidinone. The mixture was treated with a little N-methylpiperazine and heated to 80° for one hour. The mixture was decanted into water (300 ml), acidified with 5% hydrochloric acid solution and extracted with ether (3×200 ml). The aqueous phase was basified by portionwise addition of solid sodium carbonate and extracted with dichloromethane (4×150 ml). The combined and dried (Na2SO4) organic phase was filtered and concentrated to afford an oil. The oil was purified by preparative HPLC (silica gel, methanol as eluent) to give 9.84 g of the product as an oil.

Workup

  1. temperatureheated to 80° for one hour
  2. customThe mixture was decanted into water (300 ml)
  3. extractionextracted with ether (3×200 ml)
  4. additionThe aqueous phase was basified by portionwise addition of solid sodium carbonate
  5. extractionextracted with dichloromethane (4×150 ml)
  6. dry with materialdried (Na2SO4) organic phase
  7. filtrationwas filtered
  8. concentrationconcentrated
  9. customto afford an oil
  10. customThe oil was purified by preparative HPLC (silica gel, methanol as eluent)

Sources & evidence

ORD record
ord-6becfd8cdd234291bdaf0163ad97a156
Source dataset
uspto-grants-1989_05
Patent number
US04833139

Reaction notes

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