N,N-Dimethyl-1,3-propanediamine → HCID 21243697, compound

HRID 621766Notes

Reaction equation

HRID 621766 reaction equation
[C:1]([OH:16])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:17](C1NC=CN=1)(C1NC=CN=1)=O.[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33][NH2:34]>O1CCCC1>[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33][NH:34][C:1](=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:17]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 11005Myristic AcidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 21243697HCID 21243697, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.37 gm (6 meq) of myristic acid and 972 mg (6 meq) of carbonyl diimidazole are combined in a minimum volume of tetrahydrofuran and reacted at room temperature for 1 hour. 0.8 Ml (6 meq+10%) of 3-dimethylaminopropylamine is added and reacted overnight at room temperature. The reaction mixture is evaporated under reduced pressure, dried in vacuo and the desired product purified by silica gel chromatography in the system CH2Cl2 :CH3OH:NH4OH (65:25:4). Fractions 53-65 are combined, evaporated and dried in vacuo to yield 325 mg of title compound having a m.p. of 46°-48° C. after recrystallization from acetone/water.

Workup

  1. customreacted at room temperature for 1 hour
  2. customreacted overnight at room temperature
  3. customThe reaction mixture is evaporated under reduced pressure
  4. customdried in vacuo
  5. customthe desired product purified by silica gel chromatography in the system CH2Cl2 :CH3OH:NH4OH (65:25:4)
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d3868f5a9bb8497fb7679dcfde3775f2
Source dataset
uspto-grants-1989_04
Patent number
US04824996

Reaction notes

Loading…