Triethylamine → 2-[3-[[3-(Dimethylamino)propyl]amino]-3-oxopropyl]phenyl N-octadecylcarbamate

HRID 1368366Notes

Reaction equation

HRID 1368366 reaction equation
C(N(CC)CC)C.[CH2:8]([N:26]=[C:27]=[O:28])[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][CH3:25].[CH3:29][N:30]([CH3:46])[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:45])[CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[OH:44]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:8]([NH:26][C:27](=[O:28])[O:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[CH2:37][CH2:36][C:35]([NH:34][CH2:33][CH2:32][CH2:31][N:30]([CH3:29])[CH3:46])=[O:45])[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][CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66988Octadecyl isocyanateHCID 15541838HCID 15541838, compound

Product 1

HCID 98083952-[3-[[3-(Dimethylamino)propyl]amino]-3-oxopropyl]phenyl N-octadecylcarbamate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.62 ml) and octadecyl isocyanate (1.38 ml) were added to a solution containing N-[3-(dimethylamino)propyl]-3-(2-hydroxyphenyl)propanamide (1.00 g) in methylene chloride (10 ml). After being stirred for 3.5 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. The residue was purified by silica gel column chromatography (silica gel 50 g, chloroform: methanol=30: 1 to 10: 1), thereby yielding the entitled compound (1.93 g) as white solid.

Workup

  1. washwashed with saturated sodium hydrogencarbonate aqueous solution and water successively
  2. dry with materialdried over sodium sulfate anhydride
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (silica gel 50 g, chloroform: methanol=30: 1 to 10: 1)

Sources & evidence

ORD record
ord-55bbddce8b974eddae3e27fab520080e
Source dataset
uspto-grants-2003_06
Patent number
US06573297B2

Reaction notes

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