4,4-Diphenylpiperidine → HCID 9909348, compound

HRID 413284Notes

Reaction equation

HRID 413284 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([CH:13]=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([C:21]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([BH3-])#N.[Na+]>C(O)C>[CH2:1]([N:8]1[CH:12]=[CH:11][C:10]([CH2:13][N:24]2[CH2:25][CH2:26][C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][CH2:23]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 28232394,4-DiphenylpiperidineHCID 5003444Sodium cyanoborohydrideHCID 114011991-benzyl-1H-pyrazole-3-carbaldehyde

Product 1

HCID 9909348HCID 9909348, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The product from step (a) (0.17 g) was dissolved in ethanol (3 ml) and a solution of 4,4-diphenylpiperidine (0.118 g) in ethanol (1 ml) added. A solution of sodium cyanoborohydride (1.0 M in tetrahydrofuran, 3.0 ml) was added and the solution stirred at room temperature for 16 hours. Silica gel was added, the solvent removed by evaporation and the crude material purified by chromatography (dichloromethane:methanol, 100:0 to 95:5) to give the product as an oil. Further purification by supercritical fluid chromatography gave the product as a solid (0.010 g), m.p. 167-168° C.

Workup

  1. additionSilica gel was added
  2. customthe solvent removed by evaporation
  3. customthe crude material purified by chromatography (dichloromethane:methanol, 100:0 to 95:5)

Sources & evidence

ORD record
ord-6483d77b263248aa82bdfde61fb0eab7
Source dataset
uspto-grants-2003_05
Patent number
US06566376B1

Reaction notes

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