Vinylene carbonate → HCID 14685514、化合物

HRID 1073116

反応式

HRID 1073116 の反応式
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([NH2:11])=[O:10])[CH2:2]2.C1(=O)O[CH:15]=[CH:14]O1>>[O:10]1[CH:15]=[CH:14][N:11]=[C:9]1[CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1

参加物

3

反応物 2

HCID 13385Vinylene carbonateHCID 12603058Quinuclidine, 3-carbamoyl-

生成物 1

HCID 14685514HCID 14685514、化合物収率 28%

実験手順

A stirred mixture of (±) 1-azabicyclo[2.2.2]octane-3-carboxamide (D2) (2.3 g; 0.015 moles) and vinylene carbonate (1.33 g; 0.016 moles) in polyphosphoric acid was placed in an oil bath at 120° and the temperature was raised to 180° over a period of 45 min. After cooling the reaction was treated with ice and washed with ether (100 ml). The pH of the aqueous solution was adjusted to 9 with 40% sodium hydroxide and potassium carbonate was then added until saturation point. Extraction with ether (4×100 ml) followed by drying (Na2SO4) and concentration in vacuo afforded a crude oil (1.45 g). Purification on neutral alumina (Brockmann grade 1) using a graded eluant of 2%-6% methanol in ethyl acetate produced the title compound as a pale yellow oil (0.74 g; 28%) which was converted into the oxalate salt, m.p. 98°-101° C. (acetone-methanol).

後処理

  1. customwas placed in an oil bath at 120°
  2. temperaturethe temperature was raised to 180° over a period of 45 min
  3. temperatureAfter cooling the reaction
  4. additionwas treated with ice
  5. washwashed with ether (100 ml)
  6. additionwas then added until saturation point
  7. extractionExtraction with ether (4×100 ml)
  8. customby drying
  9. concentration(Na2SO4) and concentration in vacuo
  10. customafforded a crude oil (1.45 g)
  11. customPurification on neutral alumina (Brockmann grade 1)

出典と根拠

ORDレコード
ord-5cdaf1c614934df68ec44f7fee454376
出典データセット
uspto-grants-1990_11
特許番号
US04968691

関連ノート

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