Formic Acid → HCID 14987947, compound

HRID 1494271Notes

Reaction equation

HRID 1494271 reaction equation
[N:1]1([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C=O.[CH:20](O)=O>O>[CH3:20][N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 149879463-Pyridinecarboxylic acid, 6-(hexahydro-1H-1,4-diazepin-1-yl)-, methyl ester2×

Product 1

HCID 14987947HCID 14987947, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.50 g of methyl 6-homopiperazinylnicotinate (compound 13), 0.68 g of 35% formaldehyde and 1.2 g of formic acid was stirred at 70°-80° C. for 2 hours. The resulting mixture was poured into 120 ml of water and extracted with ethyl acetate. The extract was washed twice with water and once with a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate and concentrated. Purification of the concentrate by column chromatography (silica gel; ethyl acetate : methanol=1:2) gave 1.35 g of methyl 6-(4-methyl-1-homopiperazinyl)nicotinate (yield 85%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed twice with water and once with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customPurification of the
  6. concentrationconcentrate by column chromatography (silica gel; ethyl acetate : methanol=1:2)

Sources & evidence

ORD record
ord-dbb5e368442f49fa80083080ebf61136
Source dataset
uspto-grants-1991_06
Patent number
US05025012

Reaction notes

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