Potassium Carbonate → HCID 18403321, compound

HRID 1726002Notes

Reaction equation

HRID 1726002 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1C(=O)C2=CC=CC=C2C1=O.[CH:16]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:16]1([N:21]2[CH2:22][CH2:23][N:24]([CH2:2][CH2:3][CH2:4][NH2:5])[CH2:25][CH2:26]2)[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 8064211-Cyclopentylpiperazine

Product 1

HCID 18403321HCID 18403321, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(3-bromopropyl)phthalimide (0.8 g, 3.0 mmol), 1-cyclopentylpiperazine (0.46 g, 3.0 mmol), and K2CO3 (1.66 g, 12.0 mmol) in CH3CN (30 mL) was heated to reflux for 3 hours, cooled to room temperature, and filtered through diatomaceous earth (Celite®). The filtrate was concentrated, treated with 6N HCl (9.0 mL) and acetic acid (18.0 mL), heated to reflux overnight, and concentrated. The residue was treated with potassium carbonate (1.66 g) in CH3CN (30 mL) for 1 hour. After filtration of the solid, the solvent was evaporated to provide the desired product. MS (DCI/NH3) m/e 212 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.04 (br s, 2H), 3.68 (m, 4H), 3.41 (m, 4H), 3.21 (m, 2H), 2.91 (m, 2H), 2.0 (m, 4H), 1.84-1.73 (m, 4H), 1.55 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered through diatomaceous earth (Celite®)
  4. concentrationThe filtrate was concentrated
  5. additiontreated with 6N HCl (9.0 mL) and acetic acid (18.0 mL)
  6. temperatureheated
  7. temperatureto reflux overnight
  8. concentrationconcentrated
  9. additionThe residue was treated with potassium carbonate (1.66 g) in CH3CN (30 mL) for 1 hour
  10. filtrationAfter filtration of the solid
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cebd07e99f274d8ca9cd5007a17ced62
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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