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

HRID 1250779Notes

Reaction equation

HRID 1250779 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][C:37]([N:39]1[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]1)=[O:38]>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][C:37]([N:39]1[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]1)=[O:38])[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 18520258HCID 18520258, compound

Product 1

HCID 185202532-[2-(4-Methylpiperazino)-2-oxoethyl]phenyl N-octadecylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.06 ml) and octadecyl isocyanate (2.35 ml) were added to a solution containing 2-(2-hydroxyphenyl)-1-(4-methylpiperazino)-1-ethanone (1.60 g) in methylene chloride (16 ml) and stirred for 15.5 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 100 g, chloroform:methanol=50:1 to 30:1), thereby yielding the entitled compound (3.23 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 100 g, chloroform:methanol=50:1 to 30:1)

Sources & evidence

ORD record
ord-a2ec2b0c41fe480ca06d4047fc235ee7
Source dataset
uspto-grants-2002_01
Patent number
US06339154B1

Reaction notes

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