3-Chloro-4-methylphenyl isocyanate → HCID 131724571, compound

HRID 1837504Notes

Reaction equation

HRID 1837504 reaction equation
[C:1]([O-:5])([CH3:4])([CH3:3])[CH3:2].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]2)[CH:12]=1.[Cl:24][C:25]1[CH:26]=[C:27]([N:32]=[C:33]=[O:34])[CH:28]=[CH:29][C:30]=1[CH3:31]>C1(C)C=CC=CC=1>[C:1]([O-:5])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][C:30]=1[CH3:31])[NH:32][C:33]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]2)[CH:12]=1)=[O:34]

Participants

4

Reactant 2

HCID 628323-Chloro-4-methylphenyl isocyanateHCID 131724572HCID 131724572, compound

Product 1

HCID 131724571HCID 131724571, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 34.4 mmol (10 g) of 4-(5-amino-2-methoxyphenyl)piperazine-1-carboxylic acid tert-butanolate (described in J. Med. Chem., 1999, p.202) and 37.8 mmol (5.9 g) of 3-chloro-4-methylphenyl isocyanate in 150 ml of toluene is heated at reflux for 2 hours. The reaction mixture is concentrated, and the residue is taken up in 200 ml of 4N hydrochloric acid and then heated at reflux for 4 hours. After cooling, the precipitate formed is filtered off and treated with a 2N sodium hydroxide solution in order to regenerate the corresponding base.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction mixture is concentrated
  3. temperatureheated
  4. temperatureat reflux for 4 hours
  5. temperatureAfter cooling
  6. customthe precipitate formed
  7. filtrationis filtered off
  8. additiontreated with a 2N sodium hydroxide solution in order

Sources & evidence

ORD record
ord-5acabbbb4e754c72936b89ce633d64a5
Source dataset
uspto-grants-2004_08
Patent number
US06784183B2

Reaction notes

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