1-Naphthol → Propranolol

HRID 328884

반응식

HRID 328884 반응식
[CH:1]([N:4]1[CH2:7][CH:6]([OH:8])[CH2:5]1)([CH3:3])[CH3:2].[C:9]1([OH:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[OH-].[K+]>>[C:9]1([O:19][CH2:5][CH:6]([OH:8])[CH2:7][NH:4][CH:1]([CH3:2])[CH3:3])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

참가 물질

4

반응물 3

HCID 70051-NaphtholHCID 14797Potassium HydroxideHCID 5446771-(Propan-2-yl)azetidin-3-ol

생성물 1

HCID 4946Propranolol수율 76%

반응 조건

온도
160 °C

실험 절차

To a mixture of 11.5 parts of 1-(iso-propyl)-3-azetidinol and 15.8 parts of α-naphthol 0.2 part of 182°- potassium hydroxide was added, and the mixture was heated under nitrogen gas at 160° C. for 20 hours. The reaction mixture was cooled and then extracted with ether. The ether extract was washed with 2N-NaOH aqueous solution and then with water. The liquor was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was recrystallized for cyclohexane or subjected to distillation under reduced pressure. As a result 19.6 parts of 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol having a melting point of 94°-96° C. and a boiling point of 158°-159° C. under 2.5 mm Hg were obtained. The yield was 76%. The residue of infra-red spectrum analysis of the product are as follows:

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with 2N-NaOH aqueous solution
  6. dry with materialThe liquor was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized for cyclohexane
  9. distillationsubjected to distillation under reduced pressure

출처 및 근거

ORD 기록
ord-025bd82c9fa7472a8f58d36e6a1a0b4d
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04018824

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