1-(4-Pyridyl)piperazine → HCID 18918610, compound

HRID 1291816Notes

Reaction equation

HRID 1291816 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:15])[CH2:13]Br)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[N:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C(#N)C>[N:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:23][CH2:24][N:25]([CH2:13][C:12]([N:9]3[CH2:10][CH2:11][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]3)=[O:15])[CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 23368650Ethyl 1-(bromoacetyl)piperidine-4-carboxylate

Product 1

HCID 18918610HCID 18918610, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of ethyl-1-(bromoacetyl)-piperidin-4-carboxylate (0.84 g, 3 mMoles) in acetonitrile (10 ml) was added dropwise to a stirred solution of 1-(4-pyridyl)piperazine (0.5 g, 3 mMoles) in acetonitrile (20 ml) and the resulting mixture was allowed to stand for 3 hours. The white precipitate was removed by filtration and the mother liquors were concentrated under reduced pressure to give a yellow foam. The foam was purified by chromatography (flash column made with grade III neutral alumina and eluted with a gradient of 0-1% ethanol in dichloromethane) to give the title compound (350 mg) as a colourless oil which was crystallised from cyclohexane to give colourless prisms; mp 102°-104° C.; Microanalysis, found: C,63.5; H,8.1; N, 15.5%; C19H28N4O3 requires C,63.3; H,7.8; N,15.5%; NMR (d6DMSO+CD3COOD): 1.2 (t,3H), 1.3-1.7 (m,2H), 1.8 (m,2H), 2.5-2.8 (m,6H), 3.0-3.4 (m,3H), 3.6 (br s,4H), 3.9 (d,1H), 4.0 (q,2H), 4.2 (d,1H), 7.1 (d,2H), 8.2 (d,2H); m/e 361 (M+H)+.

Workup

  1. customThe white precipitate was removed by filtration
  2. concentrationthe mother liquors were concentrated under reduced pressure
  3. customto give a yellow foam
  4. customThe foam was purified by chromatography (flash column
  5. washeluted with a gradient of 0-1% ethanol in dichloromethane)

Sources & evidence

ORD record
ord-7cda7a5650da46c0823122b620fb852c
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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