Hydrochloric Acid → HCID 13336318, compound

HRID 638191Notes

Reaction equation

HRID 638191 reaction equation
[NH:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#N.Cl.[OH2:25]>C1(C)C=CC=CC=1.B(Cl)(Cl)Cl>[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]([C:7]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:1][CH:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1)=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 133912-ChlorobenzonitrileHCID 896421-Methyl-N-phenylpiperidin-4-amine

Product 1

HCID 13336318HCID 13336318, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 25135Boron TrichlorideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
150 °C

Procedure

To a 2.03M solution of boron trichloride (25×1.2 mmol) in toluene (14.8 ml) is dropwise added a solution of 4-anilino-1-methylpiperidine (4.79 g, 25 mmol) in toluene (40 ml) under ice cooling and stirring, and the resultant mixture is refluxed under stirring over a period of 1 hour. The toluene is evaporated under atmospheric pressure from the reaction mixture, and the residue is mixed with 2-chlorobenzonitrile (6.88 g, 25×2 mmol) and heated at 150° C. (bath temp.) over a period of 15 hours under stirring. After cooling, the reaction mixture is mixed with 2N hydrochloric acid (15 ml) and water (30 ml) and heated at 100° C. under stirring over a period of 20 minutes. After cooling, the reaction mixture is washed with ether, and the aqueous layer is neutralized with conc. aqueous ammoniac solution and shaken with methylene chloride. The methylene chloride layer is dried over anhydrous potassium carbonate and concentrated in vacuo. The residue is chromatographed on a column of alumina, which is eluted with methylene chloride. The eluate is concentrated, and the residue is crystallized from ether-petroleum ether to give 4-[2-(2-chlorobenzoyl)anilino]-1-methylpiperidine (8.15 g) as crystals melting at 128° to 129° C. The yield is 99%.

Workup

  1. stirringunder stirring over a period of 1 hour
  2. customThe toluene is evaporated under atmospheric pressure from the reaction mixture
  3. stirringunder stirring
  4. temperatureAfter cooling
  5. temperatureheated at 100° C.
  6. stirringunder stirring over a period of 20 minutes
  7. temperatureAfter cooling
  8. washthe reaction mixture is washed with ether
  9. stirringshaken with methylene chloride
  10. dry with materialThe methylene chloride layer is dried over anhydrous potassium carbonate
  11. concentrationconcentrated in vacuo
  12. customThe residue is chromatographed on a column of alumina, which
  13. washis eluted with methylene chloride
  14. concentrationThe eluate is concentrated
  15. customthe residue is crystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-a17a87f255024f56b69bac3cfbb33d7c
Source dataset
uspto-grants-1985_12
Patent number
US04560684

Reaction notes

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