Triethylamine → HCID 15518369, compound

HRID 1532641Notes

Reaction equation

HRID 1532641 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:21])[CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:15]([NH2:20])=[CH:16][CH:17]=[CH:18][CH:19]=1.[C:22](Cl)(=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>C(Cl)(Cl)Cl>[CH3:21][N:9]([CH3:8])[CH2:10][CH2:11][CH2:12][N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]=[C:35]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66986Myristoyl chlorideHCID 14174121N~1~-[3-(Dimethylamino)propyl]benzene-1,2-diamine

Product 1

HCID 15518369HCID 15518369, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethylamine (0.80 ml) was added to a solution containing N-[3-(dimethylamino)propyl]-1,2-benzenediamine (1.00 g) in chloroform (10 ml), and then tetradecanoyl chloride (1.42 ml) was added thereto while being cooled with ice. After being stirred for 3 hours at room temperature, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (4.3 ml) was added to a solution containing the residue (2.29 g) in ethanol (23 ml). After being stirred for 1.5 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (2.18 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1), thereby yielding the entitled compound (1.38 g) as pale brown wax.

Workup

  1. temperaturewhile being cooled with ice
  2. washwashed with saturated sodium hydrogencarbonate aqueous solution and water successively
  3. dry with materialdried over sodium sulfate anhydride
  4. concentrationconcentrated
  5. additionConcentrated hydrochloric acid (4.3 ml) was added to a solution
  6. additioncontaining the residue (2.29 g) in ethanol (23 ml)
  7. stirringAfter being stirred for 1.5 hours at 90° C.
  8. concentrationthe reaction mixture was concentrated
  9. additionThe residue, with ethyl acetate added
  10. washwas washed with 1N sodium hydroxide aqueous solution and saturated brine successively
  11. dry with materialdried over sodium sulfate anhydride
  12. concentrationconcentrated
  13. customThe residue (2.18 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-26a65c07528246d881421e59e0fa8f53
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

Loading…