Ethanol → 2-(4-[4-Methoxyphenyl]piperazin-1-yl)-5-phenoxycarbonylaminopyridine

HRID 1493593Notes

Reaction equation

HRID 1493593 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31].C(O)C>C(Cl)Cl>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:30]([O:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:31])=[CH:7][N:6]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 91616505-Amino-2-(4-[4-methoxyphenyl]piperazin-1-yl)pyridine

Product 1

HCID 149868892-(4-[4-Methoxyphenyl]piperazin-1-yl)-5-phenoxycarbonylaminopyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the product of part (ii) (1.2 g, 4.2 mmole) and triethylamine (0.5 g, 5 mmole) in methylene chloride (20 ml) was added, dropwise, phenyl chloroformate (0.8 g, 5.1 mmole) and the resulting mixture was stirred at room temperature for 20 hours. The reaction was quenched by the addition of water, the aqueous phase separated and re-extracted with methylene chloride. The combined organic extracts were washed with aqueous sodium bicarbonate solution then water, dried over magnesium sulphate and concentrated under reduced pressure to provide a solid. Trituration of this solid material with ethanol yielded the desired product, m.p. 197°-198° (1.4 g, 83%), which was used without further purification.

Workup

  1. additionwas added
  2. customThe reaction was quenched by the addition of water
  3. customthe aqueous phase separated
  4. extractionre-extracted with methylene chloride
  5. washThe combined organic extracts were washed with aqueous sodium bicarbonate solution
  6. dry with materialwater, dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customto provide a solid

Sources & evidence

ORD record
ord-f888aa0daee24a2495c91f58190ffbdc
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

Loading…