N,N-Diethyl-1,3-propanediamine → 1-(4-Chloropyridin-2-yl)-3-(3-diethylaminopropyl)urea

HRID 2215580Notes

Reaction equation

HRID 2215580 reaction equation
C1(OC(=O)[N:9]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][N:20]=2)[C:10]([O:12]C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32][NH2:33])[CH3:28]>CN(C)C=O>[Cl:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([NH:9][C:10]([NH:33][CH2:32][CH2:31][CH2:30][N:29]([CH2:34][CH3:35])[CH2:27][CH3:28])=[O:12])[CH:24]=1

Participants

4

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 21054897Phenyl (4-chloropyridin-2-yl)-N-(phenoxycarbonyl)carbamate

Product 1

HCID 219490931-(4-Chloropyridin-2-yl)-3-(3-diethylaminopropyl)ureaYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenyl(4-chloropyridin-2-yl)-N-(phenoxycarbonyl)carbamate (738 mg, 2.00 mmol) was dissolved in N,N-dimethylformamide (8.0 ml); N,N-diethyl-1,3-diaminopropane (1.57 ml, 10.0 mmol) was added thereto; and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between water and ethyl acetate; and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system) to yield the title compound (309 mg, 1.09 mmol, 54.3%) as a pale brown oil.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washand the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-b2d57b0db43d419c90334ae4babe0c6f
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

Loading…