2-[(Benzylmethylamino)methyl]-1-pyridin-3-ylcyclohexanol hydrochloride → 2-Methylaminomethyl-1-pyridin-3-yl-cyclohexanol hydrochloride

HRID 131526Notes

Reaction equation

HRID 131526 reaction equation
[ClH:1].C([CH2:9][NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[OH:18])C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[ClH:1].[CH3:9][NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[OH:18]

Participants

5

Reactant 2

HCID 692216432-[(Benzylmethylamino)methyl]-1-pyridin-3-ylcyclohexanol hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 692224012-Methylaminomethyl-1-pyridin-3-yl-cyclohexanol hydrochlorideYield 75.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

11.1 g 2-[(benzylmethylamino)methyl]-1-pyridin-3-yl-cyclohexanol hydrochloride were dissolved in 110 ml glacial acetic acid under nitrogen, 2.0 g palladium-on-active charcoal (10 percent by weight) were added as a catalyst and the mixture was stirred under a hydrogen pressure of 2.0 bar until the uptake of hydrogen had ended. The mixture was filtered with suction, the filtrate was concentrated, the residue was stirred overnight with 75 ml isopropanol and the precipitate obtained was filtered off with suction and dried. 6.18 g 2-methylaminomethyl-1-pyridin-3-yl-cyclohexanol hydrochloride were obtained.

Workup

  1. filtrationThe mixture was filtered with suction
  2. concentrationthe filtrate was concentrated
  3. customthe precipitate obtained
  4. filtrationwas filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-8402a9c933c44beea814ede68bde611e
Source dataset
uspto-grants-2008_06
Patent number
US07384961B2

Reaction notes

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