Sodium Iodide → HCID 59708792, compound

HRID 1097299Notes

Reaction equation

HRID 1097299 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:27]([O:29][C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34]Br)[CH3:28]>CC(C)=O>[CH2:27]([O:29][C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][N:15]1[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:18])[CH2:13][CH2:14]1)[CH3:28]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 41346911-(4-Boc-aminobutyl)piperazine

Product 1

HCID 59708792HCID 59708792, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (4-piperazin-1-yl-butyl)carbamic acid tert-butyl ester (17) (1.94 g, 7.54 mmol), sodium iodide (1.13 g, 7.54 mmol), potassium carbonate (3.13 g, 22.61 mmol), and 5-bromopentanoic acid ethyl ester (1.55 mL, 9.80 mmol) in acetone (60 mL) was stirred at reflux for 24 h. After removal of solvent by rotary evaporation, the resulting residue was diluted with dichloromethane and insoluble inorganics were filtered off. The liquid filtrate was concentrated in vacuo and the resulting residue was purified by Biotage silica gel column chromatography using methanol/dichloromethane (gradient 0% to 5%) to give a yellow oil, which was further purified by Biotage chromatography using ethyl acetate/dichloromethane (gradient 30% to 99%) to afford 18 as a yellow oil (1.62 g, 56%): 1H NMR (500 MHz, CDCl3) δ 1.27 (t, 3H), 1.43 (s, 9H), 1.52 (m, 6H), 1.65 (m, 2H), 2.34 (m, 6H), 2.48 (m, 6H), 3.11 (m, 2H), 4.12 (q, 2H), 5.21 (br, 1H); ESI MS m/z 386 [C20H39N3O4+H]+.

Workup

  1. temperatureat reflux for 24 h
  2. customAfter removal of solvent
  3. customby rotary evaporation
  4. additionthe resulting residue was diluted with dichloromethane and insoluble inorganics
  5. filtrationwere filtered off
  6. concentrationThe liquid filtrate was concentrated in vacuo
  7. customthe resulting residue was purified by Biotage silica gel column chromatography
  8. customto give a yellow oil, which
  9. customwas further purified by Biotage chromatography

Sources & evidence

ORD record
ord-f132e485dd4f4bdb8c4ad3331068733c
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

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