4-(2-Pyrimidinyl)-1-piperazinebutanamine → 3-(4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl)-3-azabicyclo[3.2.2]nonan-2,4-dione

HRID 4922

Reaction equation

HRID 4922 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1.[CH:18]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C:21](=[O:27])[O:20][C:19]2=O>>[N:17]1[CH:16]=[CH:15][CH:14]=[N:13][C:12]=1[N:9]1[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:1]2[C:19](=[O:20])[CH:18]3[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]3)[C:21]2=[O:27])[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamineHCID 140971693-Oxabicyclo[3.2.2]nonane-2,4-dione3×

Product 1

HCID 197971973-(4-[4-(2-Pyrimidinyl)-1-piperazinyl]butyl)-3-azabicyclo[3.2.2]nonan-2,4-dioneYield 8.7%

Procedure

An intimate mixture of 0.5 g (2.14 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine and 0.22 g (1.42 mmol) of 3-oxabicyclo[3.2.2]nonan-2,4-dione was heated in an oil bath at 220°-230° C. for 15 minutes. An additional 0.22 g (1.42 mmol) of 3-oxabicyclo[3.2.2]nonan-2,4-dione was added. Heating in an oil bath at 220°-230° C. was continued for 15 minutes and then an additional 0.22 g (1.42 mmol) of 3-oxabicyclo[3.2.2]-nonan-2,4-dione was added. Heating was continued for 30 minutes at 220°-230° C. and then the reaction mixture was cooled. The resulting product was chromatographed on silica gel, eluting with dichloromethane/methanol (96:4 followed by 94:6), to give 46 mg of the title compound (6% yield).

Workup

  1. temperaturewas heated in an oil bath at 220°-230° C. for 15 minutes
  2. temperatureHeating in an oil bath at 220°-230° C.
  3. temperatureHeating
  4. waitwas continued for 30 minutes at 220°-230° C.
  5. temperaturethe reaction mixture was cooled
  6. customThe resulting product was chromatographed on silica gel
  7. washeluting with dichloromethane/methanol (96:4 followed by 94:6)

Sources & evidence

ORD record
ord-c7add3cb537741d8851d853240637af1
Source dataset
uspto-grants-1993_09
Patent number
US05242911

Linked notes

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