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

HRID 1723491
Notes
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Reaction equation

HRID 1723491 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 filter 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 filter off
  5. washwashed with water and with 1-butanol
  6. customdried

Sources & evidence

ORD record
ord-35120250616d4775bf08c405ca5fb175
Source dataset
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04861879

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes