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1-Butanol → 1-[4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenyl]-3-methyl-2-imidazolidinone

HRID 648486
Notes
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Reaction equation

HRID 648486 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Cl)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:27][CH2:26][N:25]([CH3:28])[C:24]2=[O:29])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+].C(O)CCC>O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]2[CH2:13][CH2:14][N:16]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:27][CH2:26][N:25]([CH3:28])[C:24]4=[O:29])=[CH:21][CH:22]=3)[CH2:2][CH2:3]2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 2631-ButanolHCID 15064N,N-Bis(2-chloroethyl)-4-methoxybenzenamineHCID 516892Sodium BicarbonateHCID 223464461-(4-Aminophenyl)-3-methylimidazolidin-2-one

Product 1

HCID 137323671-[4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenyl]-3-methyl-2-imidazolidinoneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.5 parts of N,N-bis(2-chloroethyl)-4-methoxybenzenamine, 12.5 parts of 1-(4-aminophenyl)-3-methyl-2-imidazolidinone, 11 parts of sodium hydrogen carbonate and 240 parts of 1-butanol was stirred and refluxed for 24 hours. After cooling, 100 parts of water were added and the whole was stirred. The precipitated product was filtered off, washed with water and with 1-butanol and dried, yielding 17.5 parts (73%) of 1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-methyl-2-imidazolidinone; mp. 240.9°-241.0° C. (28).

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureAfter cooling
  3. stirringthe whole was stirred
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water and with 1-butanol
  6. customdried

Sources & evidence

ORD record
ord-eb8fd28dbd1b4b2a856282f00658a665
Source dataset
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04735942

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes