HCID 13812940, compound → HCID 13812944, compound

HRID 4100Notes

Reaction equation

HRID 4100 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]2[C:26]3[C:21](=[CH:22][C:23]([Br:27])=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=O)[CH2:4][CH2:3]1>P(Cl)(Cl)(Cl)=O>[Br:27][C:23]1[CH:22]=[C:21]2[C:26]3=[C:25]([CH:24]=1)[C:8]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]3[CH2:18][CH2:19][CH2:20]2

Participants

3

Reactant 1

HCID 13812940HCID 13812940, compound

Product 1

HCID 13812944HCID 13812944, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A stirred mixture of 4-methyl-N-[2-(6-bromo-1,2,3,4-tetrahydro-1-quinolinyl)phenyl]piperazine-carboxamide (14.2 g, 0.0330 mole) in phosphorus oxychloride (250 ml) was heated under reflux under nitrogen for 5 hours. The reaction mixture was cooled to room temperature and excess phosphorous oxychloride was removed at aspirator pressure with heating. The residue was chilled in an ice-bath (with exclusion of moisture), and treated with ice-cold 2N sodium hydroxide solution (250 ml) and dichloromethane (500 ml). The mixture was stirred, the organic phase was separated, washed with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was digested in boiling methanol (40 ml) to afford 10.7 g (79%) of product. Recrystallization from ethanol provided the analytical sample, mp 181°-183° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 5 hours
  3. customexcess phosphorous oxychloride was removed at aspirator pressure
  4. temperaturewith heating
  5. temperatureThe residue was chilled in an ice-bath (with exclusion of moisture)
  6. additiontreated with ice-cold 2N sodium hydroxide solution (250 ml) and dichloromethane (500 ml)
  7. customthe organic phase was separated
  8. washwashed with 2N sodium hydroxide solution, twice with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4aa0b3c2bfd344ab8cd45f0cf5194902
Source dataset
uspto-grants-1988_02
Patent number
US04723003

Reaction notes

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