N-(2-Aminoethyl)piperidine → HCID 135992596, compound

HRID 1534949Notes

Reaction equation

HRID 1534949 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[O:10]=[C:11]1[NH:19][CH:18]=[N:17][C:16]2[N:15]([CH2:20][CH2:21][C:22](OCC)=[O:23])[CH:14]=[N:13][C:12]1=2>C(#N)C>[O:10]=[C:11]1[NH:19][CH:18]=[N:17][C:16]2[N:15]([CH2:20][CH2:21][C:22]([NH:1][CH2:2][CH2:3][N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)=[O:23])[CH:14]=[N:13][C:12]1=2

Participants

4

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 135992596HCID 135992596, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.500 g (3.90 mmol) of 1-(2-aminoethyl)piperidine was added to a 10 ml round bottom flask equipped with a magnetic stirring bar. The amine was heated to 100°-110° C. and 0.250 g (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added to the stirring solution. The solution was heated for one hour at which time it had solidified. The solution was allowed to cool to room temperature and 10 ml of acetonitrile was added to the solid. This mixture was stirred and the solid was collected by Buchner vacuum filtration. The white crystalline solid was washed with acetonitrile and then with ether to yield 290 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[[2-(1-piperidinyl)]ethyl]propanaide (AIT-0070). Yield: 86%.

Workup

  1. customequipped with a magnetic stirring bar
  2. temperatureThe solution was heated for one hour at which time it
  3. filtrationthe solid was collected by Buchner vacuum filtration
  4. washThe white crystalline solid was washed with acetonitrile
  5. customwith ether to yield 290 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[[2-(1-piperidinyl)]ethyl]propanaide (AIT-0070)

Sources & evidence

ORD record
ord-852f6d3535cf4e5481ee58abfa3acc7a
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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