4-Benzylpiperidine → HCID 19598360, compound

HRID 2260794Notes

Reaction equation

HRID 2260794 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([BH3-])#N.[Na+]>CO>[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([CH2:12][N:24]3[CH2:25][CH2:26][CH:21]([CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:22][CH2:23]3)=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 317384-BenzylpiperidineHCID 5003444Sodium cyanoborohydrideHCID 10920962HCID 10920962, compound

Product 1

HCID 19598360HCID 19598360, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 171 mg of 1-phenyl pyrrole-3-carboxaldehyde in 1 mL of methanol was added 525 mg of 4-benzylpiperidine, 175 mg of 4-benzylpiperidine. HCl and 63 mg of sodium cyanoborohydride. The reaction mixture was stirred overnight at room temperature under an atmosphere of nitrogen. The methanol was removed by evaporation under reduced pressure and the residue was extracted into 50 mL of ethyl acetate, then washed successively with 50 mL aliquots of 10% sodium hydroxide and water. The ethyl acetate extract was dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure to yield 1-phenyl-3[(4-benzylpiperidin-1-yl)methyl]pyrrole, which was purified by chromatography on silica gel using 5% methanol in dichloromethane as elvent. On evaporation of the solvent, the free base was dissolved in ethanol and treated with 1 equivalent of maleic acid. The 1-phenyl-3[(4-benzyl-piperidin-1-yl)methyl]pyrrole maleate salt (compound 7) had a melting point of 159°-161° C.

Workup

  1. customThe methanol was removed by evaporation under reduced pressure
  2. extractionthe residue was extracted into 50 mL of ethyl acetate
  3. washwashed successively with 50 mL aliquots of 10% sodium hydroxide and water
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-8fc49281eec04bad8c917284123a94e8
Source dataset
uspto-grants-1995_12
Patent number
US05478934

Reaction notes

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