Potassium Carbonate → HCID 11326663, compound

HRID 1097292Notes

Reaction equation

HRID 1097292 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].C(=O)([O-])[O-].[K+].[K+].[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>CC(C)=O>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:10](=[O:11])[C:9]3[C:8](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]2=[O:16])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11326663HCID 11326663, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(4-Bromobutyl)phthalimide 7 (9.70 g, 34.40 mmol) was added to a suspension of potassium carbonate (8.20 g, 59.30 mmol) and piperazine-1-carboxylic acid tert-butyl ester 8 (5.00 g, 26.80 mmol) in acetone (125 mL). The mixture was heated at reflux for 14 hours. After cooling to ambient temperature, the reaction mixture was filtered and the filtrate concentrated to a waxy yellow solid. Purification by column chromatography (silica gel, gradient of 70:30 to 0:100 hexanes/ethyl acetate, v/v) gave compound 9 (8.69 g, 84%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 1.45 (s, 9H), 1.46-1.59 (m, 2H), 1.63-1.76 (m, 2H), 2.32-2.40 (m, 6H), 3.38-3.44 (m, 4H), 3.71 (t, J=6.9 Hz, 2H), 7.71-7.73 (m, 2H), 7.82-7.84 (m, 2H); ESI MS m/z 388 [C21H29N3O4+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 14 hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate concentrated to a waxy yellow solid
  5. customPurification by column chromatography (silica gel, gradient of 70:30 to 0:100 hexanes/ethyl acetate, v/v)

Sources & evidence

ORD record
ord-2e55d155a58d45a4bbb1878838ba0ff4
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

Loading…