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

HRID 465423노트

반응식

HRID 465423 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 19096565Water ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-99854ab73eda4a74a63280b14a8960e4
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153210

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