Ammonia → HCID 19874551, compound

HRID 465418Notes

Reaction equation

HRID 465418 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH:5]([OH:34])[CH2:6][NH:7][CH:8]([CH3:33])[CH2:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][C:16]2O[CH:18]=[C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:20](=[O:22])[CH:21]=2)=[CH:12][CH:11]=1.[NH3:38]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH:5]([OH:34])[CH2:6][NH:7][CH:8]([CH3:33])[CH2:9][C:10]1[CH:32]=[CH:31][C:13]([O:14][CH2:15][C:16]2[NH:38][CH:18]=[C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:20](=[O:22])[CH:21]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19874497HCID 19874497, compound

Product 1

HCID 19874551HCID 19874551, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl] phenoxymethyl]-5-benzyloxy-4H-pyran-4-one (2 g) in methanol (10 ml) was treated with ammonia solution, SG 0.88, (5 ml) and heated to 120° C. in a sealed vessel for 18 hours. After evaporation of the solvent in vacuo the residue was crystallised from ethanol to give 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]-propyl]phenoxymethyl]-5-benzyloxy-1H-pyrid-4-one (1.6 g , which was dissolved in methanol and the solution acidified with 2M hydrochloric acid solution to pH 1.5-2.0 and hydrogenated at room temperature and pressure over 10% palladium on charcoal. After filtration and evaporation of the solvent in vacuo the residue was treated with 1.2M sodium hydrogen carbonate solution (5 ml) and extracted with ethyl acetate (3×50 ml), dried (magnesium sulphate), filtered and evaporated under reduced pressure to give an oil. This was dissolved in methanol and treated with methanolic hydrogen chloride. Evaporation in vacuo gave 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-1H-pyrid-4-one dihydrochloride as a (37:63) mixture of diastereoisomers.

Workup

  1. customAfter evaporation of the solvent in vacuo the residue
  2. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-4847e199e2244a77955fe1172bd2118c
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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