1-Benzyl-4-piperidone → HCID 178429194、化合物

HRID 80821

反応式

HRID 80821 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([NH2:21])(=[O:20])[CH2:16][C:17]([CH3:19])=O.C([O-])(O)=O.[Na+]>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O.C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[N:21]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 192201-Benzyl-4-piperidoneHCID 80077AcetoacetamideHCID 516892Sodium Bicarbonate2 回

生成物 1

HCID 178429194HCID 178429194、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid溶媒

反応条件

温度
110 °C

実験手順

A mixture of 1-benzyl-4-piperidone (19.6 mL, 106 mmol), acetoacetamide (11.7 g, 116 mmol) in Eaton's reagent (40 mL) was allowed to stir at 110° C. After stirring for 18 h, the reaction mixture was cooled to rt, and then slowly poured into stirred aq NaHCO3 (150 g of NaHCO3 in 1000 mL of water. The mixture was diluted with DCM (1000 mL) and H2O (50 mL), and the two phases were separated. The products were extracted once with DCM (500 mL) from the aqueous layer. The combined organic layer was washed with brine (500 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The brown residue was triturated with acetone (200 mL). The precipitated solid was collected on a funnel, washed with acetone (100 mL), and dried under reduced pressure to give 6-benzyl-4-methyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-ol. 1H NMR (400 MHz, CDCl3) δ ppm 12.71 (br s, 1 H), 7.26-7.35 (m, 5 H), 6.22 (s, 1 H), 3.71 (s, 2 H), 3.34 (s, 2 H), 2.70-2.73 (m, 2 H), 2.77-2.79 (m, 2 H), 2.03 (s, 3 H); MS (ESI+) m/z 255.42 (M+H)+.

後処理

  1. stirringAfter stirring for 18 h
  2. temperaturethe reaction mixture was cooled to rt
  3. additionslowly poured
  4. customthe two phases were separated
  5. extractionThe products were extracted once with DCM (500 mL) from the aqueous layer
  6. washThe combined organic layer was washed with brine (500 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe brown residue was triturated with acetone (200 mL)
  11. customThe precipitated solid was collected on a funnel
  12. washwashed with acetone (100 mL)
  13. customdried under reduced pressure

出典と根拠

ORDレコード
ord-7f8ebd9058c44e25a610796c4d0b6ad6
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

関連ノート

読み込み中…