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

HRID 21697

반응식

HRID 21697 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-86827cc238744f2fae0bd3fed9e2f4b6
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424433

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