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Water → 1-(4-Methylpiperazino)-3-[2-(octadecyloxy)phenyl]-1-propanone

HRID 1250772
Notes
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Reaction equation

HRID 1250772 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)=[O:13].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].O>CS(C)=O.Cl>[CH3:20][N:17]1[CH2:18][CH2:19][N:14]([C:12](=[O:13])[CH2:11][CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22])[CH2:15][CH2:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 82181-BromooctadecaneHCID 14798Sodium HydroxideHCID 185202573-(2-Hydroxyphenyl)-1-(4-methylpiperazino)-1-propanone

Product 1

HCID 98071961-(4-Methylpiperazino)-3-[2-(octadecyloxy)phenyl]-1-propanoneYield 9.3%

Reagents, catalysts & solvents 2

HCID 313
Hydrochloric Acid
Solvent
HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

10% sodium hydroxide aqueous solution (6.70 g) was added to a solution containing 3-(2-hydroxyphenyl)-1-(4-methylpiperazino)-1-propanone (2.07 g) obtained in Example 3(1) in dimethylsulfoxide (21 ml). The mixture was heated up to 80° C. and 1-bromooctadecane (2.78 g) was added thereto. After being stirred for 3.75 hours at 80° C., the reaction mixture, with water added thereto, was neutralized with IN hydrochloric acid. The deposited solid was corrected by filtration and washed with water. This solid was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=50:1 to 10:1), thereby yielding the entitled compound (0.39 g) as white solid.

Workup

  1. filtrationThe deposited solid was corrected by filtration
  2. washwashed with water
  3. customThis solid was purified by silica gel column chromatography (silica gel 100 g, chloroform:methanol=50:1 to 10:1)

Sources & evidence

ORD record
ord-cf6fb81b36834be19e3687ee0b9562cf
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06339154B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes