N,N'-Dimethylethylenediamine → HCID 58154383, compound

HRID 340632Notes

Reaction equation

HRID 340632 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[O:9]=[C:10]1[NH:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1.CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:15]2[CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:11][C:10]2=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 115221-Bromo-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 58154383HCID 58154383, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-bromo-4-iodo benzene (1.00 g, 3.53 mmol), tert-butyl 3-oxopiperazine-1-carboxylate (0.71 g, 3.53 mmol), N,N′-dimethylethane-1,2-diamine (62 mg, 0.71 mmol), CuI (0.135 g, 0.71 mmol) and K3PO4 (2.25 g, 10.6 mmol) in DMF (50 mL) was stirred at 100° C. for 3 h. The mixture was partitioned between 0.1 N HCl and 2:1 hexanes:EtOAc. The organic layer was washed with saturated aq. NaHCO3 and concentrated. Purification by chromatography on silica gel (20 to 35% EtOAc in hexanes provided the title compound: LCMS m/z 356.9 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.52 (d, J=8.7 Hz, 2 H),7.17 (d, J=8.7 Hz, 2 H),4.23 (s, 2 H), 3.77 (m, 2 H),3.70 (m, 2 H),1.48 (s, 9 H).

Workup

  1. customThe mixture was partitioned between 0.1 N HCl and 2:1 hexanes
  2. washThe organic layer was washed with saturated aq. NaHCO3
  3. concentrationconcentrated
  4. customPurification by chromatography on silica gel (20 to 35% EtOAc in hexanes

Sources & evidence

ORD record
ord-a2004ef96f714862868f041a46763760
Source dataset
uspto-grants-2014_11
Patent number
US08895583B2

Reaction notes

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