Potassium Carbonate → 4-(3-t-butylureidomethyl)-1-(N-heptylaminomethyl)benzene

HRID 1770051Notes

Reaction equation

HRID 1770051 reaction equation
[C:1]([NH:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CN(C)C=O>[C:1]([NH:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][NH:16][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 202741-IodoheptaneHCID 200967404-(3-t-Butylureidomethyl)-1-aminomethylbenzene

Product 1

HCID 200967264-(3-t-butylureidomethyl)-1-(N-heptylaminomethyl)benzeneYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.97 g 4-(3-t-butylureidomethyl)-1-aminomethylbenzene obtained in Example 8, 0.57 g anhydrous potassium carbonate and 20 ml dimethylformamide was stirred at room temperature for 30 minutes, 0.93 g 1-iodoheptane was added, and stirring was continued at room temperature for an additional three hours. After distilling off the solvent under reduced pressure, the residue was extracted with chloroform, and the extract was washed with water. The chloroform was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography, giving 0.65 g of 4-(3-t-butylureidomethyl)-1-(N-heptylaminomethyl)benzene.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for an additional three hours
  3. distillationAfter distilling off the solvent under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washthe extract was washed with water
  6. distillationThe chloroform was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9a269102a0694b1dbe9ae00c8240a19b
Source dataset
uspto-grants-1995_01
Patent number
US05384425

Reaction notes

Loading…