Pyridine → Phenyl N-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate

HRID 414242

Reaction equation

HRID 414242 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:22](Cl)(=[O:30])[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1.O(C(C)C)C(C)C>O.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7914Diisopropyl EtherHCID 15891Phenyl chloroformateHCID 154406Benzenamine, 4-(4-(4-methoxyphenyl)-1-piperazinyl)-

Product 1

HCID 981607Phenyl N-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamateYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6 parts of 4-[4-(4-methoxyphenyl)-1-piperazinyl]benzenamine, 3.6 parts of phenyl carbonochloridate, 75 parts of pyridine and 98 parts of dichloromethane was stirred and warmed till all solid entered solution. Stirring was continued for 30 minutes at room temperature. The reaction mixture was poured into 500 parts of water and 210 parts of 2,2'-oxybispropane were added. The whole was stirred for a while. The precipitated product was filtered off and crystallized from 1-butanol, yielding 5.2 parts (61%) of phenyl [4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]carbamate; mp. 204.5 (intermediate 18).

Workup

  1. temperaturewarmed till all solid
  2. stirringStirring
  3. additionwere added
  4. stirringThe whole was stirred for a while
  5. filtrationThe precipitated product was filtered off
  6. customcrystallized from 1-butanol

Sources & evidence

ORD record
ord-7e34742856264106811cee026c524991
Source dataset
uspto-grants-1988_12
Patent number
US04791111

Linked notes

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