Docosanoic Acid → 2-(2-Henicosyl-1H-benzimidazol-1-yl)-N,N-dimethyl-1-ethanamine

HRID 1532686Notes

Reaction equation

HRID 1532686 reaction equation
C(N(CC)CC)C.[C:8](O)(=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(Cl)(=O)OCC.[CH3:38][N:39]([CH3:50])[CH2:40][CH2:41][NH:42][C:43]1[C:44]([NH2:49])=[CH:45][CH:46]=[CH:47][CH:48]=1>C(Cl)(Cl)Cl>[CH2:9]([C:8]1[N:42]([CH2:41][CH2:40][N:39]([CH3:50])[CH3:38])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[N:49]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 8215Docosanoic AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 522698N-[2-(dimethylamino)ethyl]benzene-1,2-diamine

Product 1

HCID 220137572-(2-Henicosyl-1H-benzimidazol-1-yl)-N,N-dimethyl-1-ethanamineYield 65.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

Triethylamine (2.25 ml) was added to a suspension containing n-docosanoic acid (4.930 g) in chloroform (50 ml), and then ethyl chlorocarbonate (1.52 ml) was added thereto while being cooled with ice. After being stirred for 1.5 hours, a solution containing N-[2-(dimethylamino)ethyl]-1,2-benzenediamine (2.593 g) in chloroform (13 ml). After being stirred for 2.5 hours while being cooled with ice, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (12.1 ml) was added to a solution containing the residue (8.644 g) in ethanol (87 ml). After being stirred for 2.5 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 (6.90 g) was purified by silica gel column chromatography (silica gel 150 g, chloroform:methanol=60:1-30:1), thereby yielding the entitled compound (4.604 g) as pale yellow solid.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringAfter being stirred for 2.5 hours
  3. temperaturewhile being cooled with ice
  4. washwashed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  5. dry with materialdried over sodium sulfate anhydride
  6. concentrationconcentrated
  7. additionConcentrated hydrochloric acid (12.1 ml) was added to a solution
  8. additioncontaining the residue (8.644 g) in ethanol (87 ml)
  9. stirringAfter being stirred for 2.5 hours at 90° C.
  10. concentrationthe reaction mixture was concentrated
  11. additionThe residue, with ethyl acetate added
  12. washwas washed with 1N sodium hydroxide aqueous solution and saturated brine successively
  13. dry with materialdried over sodium sulfate anhydride
  14. concentrationconcentrated
  15. customThe residue (6.90 g) was purified by silica gel column chromatography (silica gel 150 g, chloroform:methanol=60:1-30:1)

Sources & evidence

ORD record
ord-f29132af25534d71b0828b5b4d83bf23
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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