Methanol → HCID 66758487, compound

HRID 242574Notes

Reaction equation

HRID 242574 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)([C:14](N)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1.[OH-:36].[NH4+].[CH3:38]O>O>[CH3:38][O:36][C:14]([C:11]1([NH:17][C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)=[O:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 69252-Methylbenzenesulfonic acidHCID 14923Ammonium HydroxideHCID 705871-Benzyl-4-((4-chlorophenyl)amino)piperidine-4-carboxamide

Product 1

HCID 66758487HCID 66758487, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-Benzyl-4-(4-chloro-phenylamino)-piperidine-4-carboxylic acid amide (1.19 g 3.46 mmol) in methanol (10 ml) in a sealed tube was added toluene sulfonic acid (2.33 g, 12.11 mmol). The reaction was heated to 120° C., and stirred at that temperature behind a blast shield for 5 days. The reaction was then allowed to cool to room temperature at which time it was worked up by diluting with water, then by adding concentrated ammonium hydroxide until the pH≈8. The mixture was extracted three times with ethyl acetate and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The yellow oil was used crude (744 mg, 60%).

Workup

  1. temperatureto cool to room temperature at which time it
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0191136063aa4e548b5be0776d39cddf
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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