Dimethylamine → 2-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one

HRID 465423Notes

Reaction equation

HRID 465423 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH:5]([OH:27])[CH2:6][NH:7][CH:8]([CH3:26])[CH2:9][C:10]1[CH:25]=[CH:24][C:13]([O:14][CH2:15][C:16]2[O:17][CH:18]=[C:19]([OH:23])[C:20](=[O:22])[CH:21]=2)=[CH:12][CH:11]=1.[CH3:31][NH:32][CH3:33].[CH2:34]=O>C(O)C.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH:5]([OH:27])[CH2:6][NH:7][CH:8]([CH3:26])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][C:16]2[O:17][C:18]([CH2:31][N:32]([CH3:34])[CH3:33])=[C:19]([OH:23])[C:20](=[O:22])[CH:21]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 198745272-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one

Product 1

HCID 198745062-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 19096565Water ethanolSolvent

Procedure

A solution of 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-4H-pyran-4-one 0.8 g) in ethanol, was added to a mixture of dimethylamine (0.28 ml of a 33% solution, in ethanol) and formaldehyde (0.175 ml of a 37% aq. solution) in ethanol:water (95:5), (50 ml), at room temperature and allowed to stand for 1h. The solvent was evaporated in vacuo, the residue was partitioned between ethyl acetate and water separated and the organic extracts dried (magnesium sulphate), filtered and evaporated to an oil which was chromatographed on silica. Elution with chloroform: methanol (95:5) gave 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-6-dimethylaminomethyl-4H-pyran-4-one (0.4 g) as a 49:51 mixture of diastereoisomers.

Workup

  1. customat room temperature
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. customseparated
  5. dry with materialthe organic extracts dried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated to an oil which
  8. customwas chromatographed on silica
  9. washElution with chloroform: methanol (95:5)

Sources & evidence

ORD record
ord-99854ab73eda4a74a63280b14a8960e4
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

Loading…