Water → 2-(Pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one

HRID 44662

반응식

HRID 44662 반응식
[OH-].[K+].Cl.[N:4]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[C:6](=[O:12])[CH2:5]2.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1.O>CO>[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[C:5]2[C:6](=[O:12])[CH:7]3[CH2:10][CH2:11][N:4]2[CH2:9][CH2:8]3)[CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 103713-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

생성물 1

HCID 6118222-(Pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one수율 76.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Potassium hydroxide (56 g, 0.54 mole) was dissolved in methanol (420 mL). 3-Quinuclidinone hydrochloride (75 g, 0.49 mole) was added and the mixture was stirred for 30 min at ambient temperature. 3-Pyridinecarboxaldehyde (58 g, 0.54 mole) was added and the mixture stirred for 16 h at ambient temperature. The reaction mixture became yellow during this period, with solids caking on the walls of the flask. The solids were scraped from the walls and the chunks broken up. With rapid stirring, water (390 mL) was added. When the solids dissolved, the mixture was cooled at 4° C. overnight. The crystals were collected by filtration, washed with water, and air dried to obtain 80 g of yellow solid. A second crop (8 g) was obtained by concentration of the filtrate to ˜10% of its former volume and cooling at 4° C. overnight. Both crops were sufficiently pure for further transformation (88 g, 82%).

후처리

  1. stirringthe mixture stirred for 16 h at ambient temperature
  2. waitThe reaction mixture became yellow during this period, with solids
  3. dissolutionWhen the solids dissolved
  4. temperaturethe mixture was cooled at 4° C. overnight
  5. filtrationThe crystals were collected by filtration
  6. washwashed with water, and air
  7. customdried

출처 및 근거

ORD 기록
ord-574dad82290847ed9ae69fd9e47196fb
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541447B2

연결된 노트

불러오는 중…