Hydrochloric Acid → 4-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)piperidine

HRID 2255144

반응식

HRID 2255144 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][OH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH:14]1[CH2:19][CH2:18][CH:17]([C:20](=O)[CH3:21])[CH2:16][CH2:15]1.Cl>C(O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:20]([CH:17]3[CH2:18][CH2:19][NH:14][CH2:15][CH2:16]3)([CH3:21])[O:13][CH2:12][CH2:11][C:5]=2[CH:4]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 819113,4-Dimethoxyphenethyl alcoholHCID 27237641-(Piperidin-4-yl)ethan-1-one

생성물 1

HCID 200879464-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)piperidine수율 86%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 200 g of 3,4-dimethoxybenzeneethanol and 163,7 g of 1-(4-piperidinyl)ethanone in 800 ml of ethanol saturated with anhydrous hydrochloric acid was stirred for 15 h at ambient temperature. The mixture was concentrated under vacuum, and the concentrate was diluted with 500 ml of ethanol after which the hydrochloride precipitated. After filtration the hydrochloride was dissolved in water and sodium hydroxide until the pH was 12. The base was extracted with dichloromethane, and the organic phase was washed with water, dried and evaporated to yield 251 g (86,5%) of crude 4-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)piperidine.

후처리

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe concentrate was diluted with 500 ml of ethanol after which the hydrochloride
  3. customprecipitated
  4. filtrationAfter filtration the hydrochloride
  5. dissolutionwas dissolved in water
  6. extractionThe base was extracted with dichloromethane
  7. washthe organic phase was washed with water
  8. customdried
  9. customevaporated

출처 및 근거

ORD 기록
ord-9f3cbcac96d64b3f8afea45a665b299c
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05238939

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