Hydrochloric Acid → HCID 23467151, compound

HRID 443411Notes

Reaction equation

HRID 443411 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9](=O)[CH3:10])=[N:6][CH:7]=1.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.Cl.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO>[CH:12]1([NH:15][CH:9]([CH3:10])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 15572420HCID 15572420, compound

Product 1

HCID 23467151HCID 23467151, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 0.8 g of 5-hydroxy-2-pyridylacetone in 25 ml of methanol, 0.33 g of cyclopropylamine, 1 ml of 5 N ethereal hydrogen chloride and 1.16 g of sodium cyanoborohydride are added in this order and the mixture is stirred at room temperature for 3 days. The pH thereof is then adjusted to 1 with 5 N ethereal hydrogen chloride, and then to 8 with solid sodium bicarbonate. The mixture is filtered, evaporated and the residue chromatographed on silica gel with ethyl acetate-methanol (4:1) as eluant, to yield 2-(2-cyclopropylaminopropyl)-5-pyridinol. It is converted into its monofumarate as shown in Example 7, melting at 161° with decomposition.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated
  3. customthe residue chromatographed on silica gel with ethyl acetate-methanol (4:1) as eluant

Sources & evidence

ORD record
ord-39e28805272a480fbbbb05d17a3c38b8
Source dataset
uspto-grants-1981_04
Patent number
US04260619

Reaction notes

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