Ammonium Hydroxide → 1-Benzyl-4-((4-fluorophenyl)amino)piperidine-4-carboxamide

HRID 1683042Notes

Reaction equation

HRID 1683042 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:24].[NH4+]>S(=O)(=O)(O)O>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)([C:14]([NH2:15])=[O:24])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 30172221-Benzyl-4-((4-fluorophenyl)amino)piperidine-4-carbonitrile

Product 1

HCID 30172231-Benzyl-4-((4-fluorophenyl)amino)piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Cautiously combine 1-benzyl-4-(4-fluoro-phenylamino)-piperidine-4-carbonitrile (60 mmol) and concentrated sulfuric acid (270 mL). Let stand for 24 h at ambient temperature. Cautiously pour the reaction mixture into excess dilute ammonium hydroxide solution/ice. Extract with dichloromethane (3×300 mL). Combine the dichloromethane extracts and extract them using saturated NaHCO3 solution (3×300 mL). Dry the dichloromethane solution over magnesium sulfate, filter, and concentrate in vacuo to obtain a residue. Purify to obtain the title compound.

Workup

  1. extractionExtract with dichloromethane (3×300 mL)
  2. extractionCombine the dichloromethane extracts and extract them
  3. dry with materialDry the dichloromethane solution over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customto obtain a residue
  7. customPurify

Sources & evidence

ORD record
ord-22fcab1673fb4909b7e0b7144d67ffbb
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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