Formaldehyde → HCID 70417761, compound

HRID 2231640Notes

Reaction equation

HRID 2231640 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([C:18]([NH:20][C:21]2[CH:26]=[N:25][CH:24]=[CH:23][N:22]=2)=[O:19])[CH2:3]1.[CH2:27]=[O:28].[OH-].[Na+]>C(O)(=O)C.O>[OH:28][CH2:27][N:12]1[C:11]2[C:17]3[C:14]([CH2:15][C@@H:16]4[C@@H:6]([C:7]=3[CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:18]([NH:20][C:21]2[CH:26]=[N:25][CH:24]=[CH:23][N:22]=2)=[O:19])[CH2:3][N:2]4[CH3:1])=[CH:13]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 70416859HCID 70416859, compound

Product 1

HCID 70417761HCID 70417761, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4 g of 6-Methyl-N-pyrazinylergoline-8β-carboxamide (see Example 1) dissolved in 42 ml of acetic acid are placed in a three-necked bottle and diluted with 200 ml of water. 42 ml of an aqueous formaldehyde solution (35% of weight) are added. The mixture is stirred for three hours at 60°-70°, cooled to 20°, adjusted to a pH-value of 8 with a 5N sodium hydroxide solution and extracted with methylene chloride. After evaporation of the solvent, 3.28 g of the obtained crude product, 1-hydroxymethyl-6-methyl-N-pyrazinylergoline-8β-carboxamide, are dissolved in 270 ml of absolute methanol after which 52 g tartaric acid is added and the mixture is stirred for three hours at 60°. The solvent is evaporated in vacuo. The residue is taken up in water, neutralized with a 2N potassiumbicarbonate solution and extracted with methylene chloride. The crude product, obtained after evaporation of the solvent, is purified by chromatography on a column of silica gel. The product is eluted with 3% methanol in methylene chloride and is dissolved in acetone. Two equivalents of tartaric acid are added to form the tartaric acid addition salt.

Workup

  1. temperaturecooled to 20°
  2. extractionextracted with methylene chloride
  3. customAfter evaporation of the solvent, 3.28 g of the

Sources & evidence

ORD record
ord-8c74ba0e33b4484dbc04658e5346e465
Source dataset
uspto-grants-1988_11
Patent number
US04783464

Reaction notes

Loading…