Hydrochloric Acid → 3-(Dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one

HRID 1110822

반응식

HRID 1110822 반응식
Cl.[CH3:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=1)=[O:4].Cl.[CH3:18][NH:19][CH3:20].[CH2:21]=O>C(O)C.CC(C)=O>[CH3:18][N:19]([CH2:21][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1)=[O:4])[CH3:20]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 712Formaldehyde2회HCID 10473Dimethylamine, hydrochlorideHCID 143453',4',5'-Trimethoxyacetophenone

생성물 1

HCID 4123063-(Dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one수율 73.3%

시약·촉매·용매 2

HCID 180Acetone용매HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

Concentrated hydrochloric acid (1 mL) was added to a stirred mixture of 3,4,5-trimethoxyacetophenone (210 g, 1 mol), dimethylamine hydrochloride (81 g, 1 mol) and paraformaldehyde (45 g, 1.5 mol) in ethanol (300 mL). The reaction mixture was heated under reflux for 1 hour. Another portion of paraformaldehyde (30 g, 1 mol) was added and the heating was continued for another 2 hours. The warm reaction mixture was poured with vigorous stirring into acetone (2.4 L). The slurry was heated at 60° C. for 15 minutes, cooled, and filtered. The solid was washed with acetone and dried to provide the hydrochloride salt of 3-(N,N-dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one (196 g, 65%): R.function.0.05 (SiO2 ; hexane-ethyl acetate, 2:1; v/v); mp 175° C. A mixture of the above hydrochloride (147.5 g, 0.48 mol) in 1N NaOH (750 mL) was shaken with ethyl acetate (4×100 mL). The combined organic extracts were washed with brine, dried, and evaporated in vacuo to give 3-(N,N-dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1 one mp 45°-47° C.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe warm reaction mixture
  4. additionwas poured
  5. temperaturecooled
  6. filtrationfiltered
  7. washThe solid was washed with acetone
  8. customdried

출처 및 근거

ORD 기록
ord-0d5769fb0259414398b321521385cbe8
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04977146

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