Triethylamine → HCID 9852040, compound

HRID 1368381Notes

Reaction equation

HRID 1368381 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].[CH2:29]([N:36]1[CH2:41][CH2:40][N:39]([C:42](=[O:52])[CH2:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[OH:51])[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[CH2:8]([NH:26][C:27](=[O:28])[O:51][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=1[CH2:44][CH2:43][C:42]([N:39]1[CH2:40][CH2:41][N:36]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:37][CH2:38]1)=[O:52])[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 18520251HCID 18520251, compound

Product 1

HCID 9852040HCID 9852040, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.84 ml) and octadecyl isocyanate (1.88 ml) were added to a solution containing 1-(4-benzylpiperazino)-3-(2-hydroxyphenyl)-1-propanone (1.76 g) in methylene chloride (18 ml) and stirred for 17 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 75 g, chloroform:methanol=60:1), thereby yielding the entitled compound (2.32 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 75 g, chloroform:methanol=60:1)

Sources & evidence

ORD record
ord-b7de514e10b642c7bfd90f37add83be0
Source dataset
uspto-grants-2003_06
Patent number
US06573297B2

Reaction notes

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