Hydrochloric Acid → HCID 66811551, compound

HRID 1099200Notes

Reaction equation

HRID 1099200 reaction equation
C1(C[NH:8][CH2:9][CH:10]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][CH2:13][CH2:12][NH:11]2)C=CC=CC=1.[ClH:22].O1CCOCC1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[Cl-:22].[Cl-:22].[NH3+:8][CH2:9][CH:10]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][NH2+:11]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 66811513HCID 66811513, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66811551HCID 66811551, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-phenyl-N-[(3-phenylpiperidin-2-yl)methyl]methanamine (101 mg, 0.359 mmol) in methanol (5 ml) were added 4M HCl in dioxane (0.090 ml, 0.359 mmol) and palladium hydroxide (28.9 mg, 0.036 mmol). The reaction mixture was charged with 1 atm hydrogen gas and allowed to stir for 18 h. The reaction mixture was filtered through celite, and to the filtrate was added 4M HCl in dioxane (0.090 ml, 0.359 mmol). The reaction was allowed to stir for 1 h and concentrated in vacuo to yield 2-(ammoniomethyl)-3-phenylpiperidinium dichloride (61%). LCMS (M+H)=191.0.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. stirringto stir for 1 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b6baeb5833b41ad83dcbed9313b8f81
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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