Water → HCID 14031837, compound

HRID 986395Notes

Reaction equation

HRID 986395 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=3[O:26][CH3:27])[CH2:15][CH2:14]2)=[N:11][CH3:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CC=CC=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:34](=[O:36])[CH3:35])=[CH:21][C:20]=3[O:26][CH3:27])[CH2:15][CH2:14]2)=[N:11][CH3:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14031836HCID 14031836, compound

Product 1

HCID 14031837HCID 14031837, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.10 mole of N-[3,5-dichlorophenyl]-N'-methyl-4-[2-methoxy-4-hydroxy phenyl]-1-piperazine-carboxamidine, 0.12 mole of pyridine and 0.12 mole of acetic anhydride in 250 ml of dichloromethane was stirred 12 hours at room temperature and poured into 2 L water. The organic phase was separated, washed with cold water, dried on sodium sulfate and evaporated. The residue (oil) was purified by flash chromatography on silica gel (200 mesh) using ethylacetate (60)/methanol (40) as eluant. The first 250 ml of eluant were collected and evaporated, and the residue further purified by recrystallization, to give N-[3,5-dichlorophenyl]-N'-methyl-4-[2-methoxy-4-acetyloxy-phenyl]-1-piperazine-carboxamidine, m.p. 144° C.

Workup

  1. customThe organic phase was separated
  2. washwashed with cold water
  3. customdried on sodium sulfate
  4. customevaporated
  5. customThe residue (oil) was purified by flash chromatography on silica gel (200 mesh)
  6. customThe first 250 ml of eluant were collected
  7. customevaporated
  8. customthe residue further purified by recrystallization

Sources & evidence

ORD record
ord-5b519eee08e44513b54f7571c5243b99
Source dataset
uspto-grants-1987_12
Patent number
US04713382

Reaction notes

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