Hydrochloric Acid → 2-Thiophenemethanamine, N,N-dimethyl-alpha-ethyl-alpha-(3-(3,4,5-trimethoxyphenyl)propyl)-

HRID 1708967노트

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HRID 1708967 반응식
[CH2:1]([C:3]([NH:24][CH3:25])([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)[CH3:2].C=O.[C:28]([BH3-])#N.[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CO>[CH2:1]([C:3]([N:24]([CH3:28])[CH3:25])([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)[CH3:2]

참가 물질

8

반응물 5

HCID 313Hydrochloric Acid2회HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 106424791-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N-methylbutylamine

생성물 1

HCID 30783212-Thiophenemethanamine, N,N-dimethyl-alpha-ethyl-alpha-(3-(3,4,5-trimethoxyphenyl)propyl)-수율 79.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

실험 절차

1.7 g of 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N-methylbutylamine are dissolved in 15 ml of acetonitrile. 1.5 ml of 35% formalin and 0.59 g of sodium cyanoborohydride are added to the solution, and the mixture is adjusted to pH 6.5 with methanol containing hydrogen chloride and stirred at room temperature for 8 hours. After the reaction, the mixture is acidified with 10% hydrochloric acid and stirred for 30 minutes. The mixture is alkalized with an aqueous 20% potassium carbonate solution and concentrated under reduced pressure. The residue is extracted with ethyl acetate, and the extract is washed with an aqueous saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:ethanol=30:1) to give 1.4 g of 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N,N-dimethylbutylamine as colorless crystals. yield; 79.3% M.p. 62°-63 ° C. (recrystallized from ether-n-hexane)

후처리

  1. customAfter the reaction
  2. stirringstirred for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue is extracted with ethyl acetate
  5. washthe extract is washed with an aqueous saturated sodium chloride solution
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethanol=30:1)

출처 및 근거

ORD 기록
ord-75a7d2a9796d418dbfa381361c9f087a
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04946862

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