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

HRID 1368369Notes

Reaction equation

HRID 1368369 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].[OH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][CH2:37][C:38]([N:40]1[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]1)=[O:39]>C(Cl)Cl>[CH2:8]([NH:26][C:27](=[O:28])[O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][CH2:37][C:38]([N:40]1[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]1)=[O:39])[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

5

Reactant 3

HCID 8471TriethylamineHCID 66988Octadecyl isocyanateHCID 185202573-(2-Hydroxyphenyl)-1-(4-methylpiperazino)-1-propanone

Product 1

HCID 98074162-[3-(4-Methylpiperazino)-3-oxopropyl]phenyl N-octadecylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.62 ml) and octadecyl isocyanate (1.40 ml) were added to a solution containing 3-(2-hydroxyphenyl)-1-(4-methylpiperazino)-1-propanone (1.00 g) in methylene chloride (10 ml) and stirred for 4 hours at room temperature. The insoluble matters were filtrated out and washed with chloroform. The filtrate and washings were combined and the mixture was 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 50 g, chloroform:methanol=50:1), thereby yielding the entitled compound (2.05 g) as white solid.

Workup

  1. filtrationThe insoluble matters were filtrated out
  2. washwashed with chloroform
  3. washthe mixture was washed with saturated sodium hydrogencarbonate aqueous solution and brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-5cd185b4afd948278dd660223ce08287
Source dataset
uspto-grants-2003_06
Patent number
US06573297B2

Reaction notes

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