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

HRID 45280

反応式

HRID 45280 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 6118222-(Pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one収率 82%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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% yield).

後処理

  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

出典と根拠

ORDレコード
ord-eb0a5e3ea8434f3c812a5c3f0a10a0b3
出典データセット
uspto-grants-2013_09
特許番号
US08541446B2

関連ノート

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