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

HRID 1250761Notes

Reaction equation

HRID 1250761 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-382172126e4142cf9a44ea4cdb43dfa7
Source dataset
uspto-grants-2002_01
Patent number
US06339154B1

Reaction notes

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