Acetone → 3-(4-Phenylpiperazin-1-yl)propan-1-amine

HRID 396659Notes

Reaction equation

HRID 396659 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.Br[CH2:15][CH2:16][CH2:17][NH2:18].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CCO>[NH2:18][CH2:17][CH2:16][CH2:15][N:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 2612973-(4-Phenylpiperazin-1-yl)propan-1-amineYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Phenylpiperazine (5.00 g, 30.8 mmol, 1.00 equiv, Aldrich), 3-bromopropylamine hydrobromide (8.09 g, 37.0 mmol, 1.20 equiv) and potassium carbonate (8.51 g, 61.6 mmol, 2.00 equiv) were stirred in refluxing acetone (200 mL) and EtOH (40 mL) for 14 hours. After removal of the solvents, water (250 mL) was added and the pH was adjusted to 11-12 by addition of 1 N aqueous NaOH. The mixture was extracted with CH2Cl2 (4×250 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, CHCl3-MeOH-NH (2 M in MeOH) 100:10:5 to 100:20:10) to give 3.80 g (56%) of yellow oil, which was characterized spectroscopically.

Workup

  1. customAfter removal of the solvents, water (250 mL)
  2. additionwas added
  3. additionthe pH was adjusted to 11-12 by addition of 1 N aqueous NaOH
  4. extractionThe mixture was extracted with CH2Cl2 (4×250 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, CHCl3-MeOH-NH (2 M in MeOH) 100:10:5 to 100:20:10)

Sources & evidence

ORD record
ord-c1ed6536eb454aa1a3021a9fd5114f59
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

Loading…