Potassium Carbonate → HCID 86681375, compound

HRID 1406678Notes

Reaction equation

HRID 1406678 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][CH2:12][CH2:11][O:10]2)=[CH:5][CH:4]=1.[N:20]1([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:14]1([C:9]2([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][N:23]4[CH2:22][CH2:21][N:20]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:25][CH2:24]4)=[CH:4][CH:5]=3)[O:13][CH2:12][CH2:11][O:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 207112Ethyl piperazine-1-acetateHCID 572491342-[4-(Bromomethyl)phenyl]-2-phenyl-1,3-dioxolane

Product 1

HCID 86681375HCID 86681375, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a round-bottom flask were added 13 (2.57 g, 8.05 mmol, 1.0 equiv.), 10 (2.09 g, 12.1 mmol, 1.5 equiv.), K2CO3 (3.35 g, 24.2 mmol, 3.0 equiv.), and acetone (40 mL, 0.2 M). The reaction mixture was stirred overnight at reflux. The reaction mixture was cooled to room temperature. The solid was filtered and washed with acetone. The filtrate was concentrated and purified by silica gel column chromatography (gradient, 50-100% EtOAc/hexanes) to yield 14 (2.54 g, 77%) as a yellow oil. 1H-NMR (500 MHz, CDCl3) δ 7.52-7.50 (m, 2H), 7.44 (d, 2H, J=8.5 Hz), 7.34-7.25 (m, 5H), 4.17 (q, 2H, J=7.0 Hz), 4.09-4.06 (m, 2H), 4.05-4.02 (m, 2H), 2.57 (br s, 4H), 2.50 (br s, 4H), 1.26 (t, 3H, J=7.0 Hz). 13C-NMR (125 MHz, CDCl3): δ 170.3, 142.1, 140.9, 137.9, 128.9, 128.1, 128.0, 126.1, 126.0, 109.4, 64.8, 62.6, 60.6, 59.5, 53.1, 52.7, 14.2.

Workup

  1. temperatureat reflux
  2. filtrationThe solid was filtered
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography (gradient, 50-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fa0346153db64cf797137199d7614d48
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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