Dodecanoyl chloride → HCID 15518368, compound

HRID 1532640Notes

Reaction equation

HRID 1532640 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][CH3:33]>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:33]1[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 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 14174121N~1~-[3-(Dimethylamino)propyl]benzene-1,2-diamine

Product 1

HCID 15518368HCID 15518368, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethylamine (0.85 ml) was added to a solution containing N-[3-(dimethylamino)propyl]-1,2-benzenediamine (1.06 g) in chloroform (11 ml) and then dodecanoyl chloride (1.28 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 (4.6 ml) was added to a solution containing the residue (2.23 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 (2.14 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=60:1), thereby yielding the entitled compound (1.33 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 (4.6 ml) was added to a solution
  6. additioncontaining the residue (2.23 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 (2.14 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=60:1)

Sources & evidence

ORD record
ord-33520e2d58f94d189259298158d5a644
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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