Hydrochloric Acid → 4-Hydroxymethyl-4-(3-methylphenylamino)-piperidine hydrochloride salt

HRID 443300Notes

Reaction equation

HRID 443300 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:22][OH:23])([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:24]>[Pd].CO>[ClH:24].[OH:23][CH2:22][C:11]1([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 211933021-Benzyl-4-hydroxymethyl-4-(3-methylphenylamino)piperidine

Product 1

HCID 211934274-Hydroxymethyl-4-(3-methylphenylamino)-piperidine hydrochloride salt

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 1-benzyl-4-hydroxymethyl-4-(3-methylphenylamino)piperidine (0.2 g, 0.64 mmol) and 10% palladium on charcoal (0.4 g) in a mixture of methanol (15 mL) and methanol saturated with anhydrous hydrochloride gas (10 mL) was shaken in a Parr hydrogenator at 60 psi for 24 h. The resultant mixture was filtered through a plug of Celite, and the filtrate was concentrated to provide the title compound.

Workup

  1. filtrationThe resultant mixture was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c985087fb1324c29b74ef706368dd371
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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