1-Benzyl-4-piperidone → 2-Amino-6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carbonitrile

HRID 21697

反応式

HRID 21697 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.[NH:15]1CCCC1.C(O[CH:23]=[C:24]([C:27]#[N:28])[C:25]#[N:26])C.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1.O1CCOCC1>[NH2:26][C:25]1[C:24]([C:27]#[N:28])=[CH:23][C:12]2[CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10][C:11]=2[N:15]=1

参加物

7

反応物 4

HCID 192201-Benzyl-4-piperidoneHCID 31268PyrrolidineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 517165Ammonium Acetate

生成物 1

HCID 110545552-Amino-6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carbonitrile収率 49.5%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 1-benzyl-4-piperidone (26.8 g, 0.14 mole) and pyrrolidine (20 g, 0.28 mole) in toluene (300 ml) is refluxed for 4 hours with distilling off water. The reaction solution is concentrated to dryness under reduced pressure, and to the residue is added anhydrous dioxane (300 ml). To the mixture is added dropwise gradually with stirring a solution of ethoxymethylenemalononitrile (19 g, 0.16 mole) in anhydrous dioxane (40 ml) under ice-cooling. The mixture is warmed to room temperature, and stirred for one hour. To the mixture is added ammonium acetate (22 g, 0.29 mole), and the mixture is stirred at 70° C. overnight, and concentrated to dryness under reduced pressure. To the residue is added isopropanol, and the precipitate crystals are collected by filtration, washed with water, and dried to give 2-amino-6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine-3-carbonitrile (18.3 g, yield; 49%), which is used in the subsequent reaction without purification.

後処理

  1. distillationwith distilling off water
  2. concentrationThe reaction solution is concentrated to dryness under reduced pressure
  3. additionto the residue is added anhydrous dioxane (300 ml)
  4. additionTo the mixture is added dropwise gradually
  5. temperaturecooling
  6. stirringthe mixture is stirred at 70° C. overnight
  7. concentrationconcentrated to dryness under reduced pressure
  8. additionTo the residue is added isopropanol
  9. filtrationthe precipitate crystals are collected by filtration
  10. washwashed with water
  11. customdried

出典と根拠

ORDレコード
ord-86827cc238744f2fae0bd3fed9e2f4b6
出典データセット
uspto-grants-1995_06
特許番号
US05424433

関連ノート

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