Nitrogen → HCID 20117407, compound

HRID 1044800Notes

Reaction equation

HRID 1044800 reaction equation
N#N.[C:3]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:5])[CH3:4].[CH2:12]1CCN2[C:15](=[N:16]CCC2)[CH2:14][CH2:13]1.BrCCCC#N>CCOCC>[NH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:9]1[CH2:10][CH2:11][N:6]([C:3](=[O:5])[CH3:4])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 214124-BromobutyronitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 837951-Acetylpiperazine

Product 1

HCID 20117407HCID 20117407, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 1-acetylpiperazine (256 mg, 2.00 mmol) and DBU (0.30 mL, 2.00 mmol) in dry Et2O (2 mL) was added 4-bromobutyronitrile (0.21 mL, 2.00 mmol) at 0° C. The reaction mixture was stirred at rt until completion of the reaction. The mixture was filtered and concentrated under reduced pressure. A 0.087 mol/L solution of the crude nitrile in EtOH (10 mL) was hydrogenated at 50° C. using the H-Cube® (1 mL/min) with a Raney Nickel cartridge (30 mm) under 50 bar until completion of the reaction. The solution was then concentrated under reduced pressure to give crude 1-(4-(4-aminobutyl)piperazin-1-yl)ethanone as a colorless oil. GC-MS-conditions 01: tR=2.94 min; [M+H]+=200.40.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customwas hydrogenated at 50° C.
  4. customuntil completion of the reaction
  5. concentrationThe solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-23018e5d8d9d4195b05ffcdcd01e6233
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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