N,N'-Dimethylethylenediamine → HCID 59485614, compound

HRID 2387233Notes

Reaction equation

HRID 2387233 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:16]1[CH:20]=[CH:19][S:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>O1CCOCC1.CCOC(C)=O.[Cu]I>[O:14]=[C:10]1[N:11]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 133833-BromothiopheneHCID 62657Potassium Phosphate, TribasicHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 59485614HCID 59485614, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-Boc-3-oxopiperazine (1.0 eq.), 3-bromothiophene (1.5 eq.), K3PO4(2.0 eq.), CuI (0.4 eq.) and N,N′-dimethylethylendiamine (0.8 eq.) in 1,4-dioxane (0.5M) was put in a sealed vial and stirred at 110° C. for 18 hr. Reaction mixture was diluted with EtOAc and filtered through a pad of SolcaFloc® 200 FCC. After removal of the solvent, the crude product was purified by flash column chromatography on silica gel using 10-40% EtOAc/Petroleum ether as eluent to afford the desired product H1 as pink solid (80% yield). 1H NMR (400 MHz, CDCl3, 300K) δ 7.32-7.28 (3H, m), 4.25 (2H, s), 3.82-3.75 (4H, m), 1.49 (9H, s). MS (ES) C13H18N2O3S requires: 282, found: 283 (M+H)+.

Workup

  1. customReaction mixture
  2. filtrationfiltered through a pad of SolcaFloc® 200 FCC
  3. customAfter removal of the solvent
  4. customthe crude product was purified by flash column chromatography on silica gel using 10-40% EtOAc/Petroleum ether as eluent

Sources & evidence

ORD record
ord-da140da32c934f89bdfaf5d0b202bf1f
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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