Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride → 6-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one

HRID 241837

反応式

HRID 241837 の反応式
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16]([O:18]CC)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)C.[CH:25]([NH2:27])=[NH:26].C[O-].[Na+]>CO>[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2[N:26]=[CH:25][NH:27][C:16](=[O:18])[C:11]=2[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 102623Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 160693Formamidine acetateHCID 10942334Sodium Methoxide

生成物 1

HCID 1355929356-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one収率 64.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
85 °C

実験手順

A mixture of ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (50.0 g, 0.168 mol), formamidine acetate (16.2 g, 0.201 mol), 4.37 M of sodium methoxide in methanol (190 mL) and methanol (200 mL) was heated at 85° C. for 16 hour in a 350 mL sealed reaction vessel. The mixture was allowed to cool and concentrated in vacuo. The residue was dissolved in 1N NaOH (150 mL) and poured over ice. Glacial acetic acid was added to the mixture until the pH of the mixture was 7 and a tan solid precipitated out. The solid was filtered, washed with water and cold ether, and dried on high vacuum to yield the title compound as a tan solid (26.2 g, 61.4%).

後処理

  1. customsealed
  2. customreaction vessel
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 1N NaOH (150 mL)
  6. additionpoured over ice
  7. additionGlacial acetic acid was added to the mixture until the pH of the mixture
  8. customa tan solid precipitated out
  9. filtrationThe solid was filtered
  10. washwashed with water and cold ether
  11. customdried on high vacuum

出典と根拠

ORDレコード
ord-2aee3a8fb4a84937a78c3e3c776d8e6e
出典データセット
uspto-grants-2014_02
特許番号
US08653091B2

関連ノート

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