Triethylamine → 2-[3-(4-Methylpiperazino)-3-oxopropyl]phenyl N-tetradecylcarbamate

HRID 1368379Notes

Reaction equation

HRID 1368379 reaction equation
C(N(CC)CC)C.[CH2:8]([N:22]=[C:23]=[O:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[OH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][CH2:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]1)=[O:35]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:8]([NH:22][C:23](=[O:24])[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][CH2:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]1)=[O:35])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3485710Tetradecyl isocyanateHCID 185202573-(2-Hydroxyphenyl)-1-(4-methylpiperazino)-1-propanone

Product 1

HCID 99571202-[3-(4-Methylpiperazino)-3-oxopropyl]phenyl N-tetradecylcarbamateYield 91%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.06 ml) and tetradecyl isocyanate (1.64 g) were added to a solution containing 3-(2-hydroxyphenyl)-1-(4-methylpiperazino)-1-propanone (1.70 g) obtained in Example 3(1) in methylene chloride (17 ml). After being stirred for 18.5 hours at room temperature, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and brine successively, dried over sodium sulfate anhydride, and concentrated. The residue was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=60:1 to 30:1), thereby yielding the entitled compound (3.04 g) as white solid.

Workup

  1. washwashed with saturated sodium hydrogencarbonate aqueous solution and brine successively
  2. dry with materialdried over sodium sulfate anhydride
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=60:1 to 30:1)

Sources & evidence

ORD record
ord-126eadac0875495c96dafffcdb32606e
Source dataset
uspto-grants-2003_06
Patent number
US06573297B2

Reaction notes

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