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Water → 4-(Dimethylamino)piperidine dihydrochloride

HRID 492851
Notes
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Reaction equation

HRID 492851 reaction equation
[ClH:1].Cl.[CH3:3][N:4]([CH3:18])[CH:5]1[CH2:10][CH2:9][N:8](CC2C=CC=CC=2)[CH2:7][CH2:6]1.O>CC(O)C.[C].[Pd]>[ClH:1].[ClH:1].[CH3:3][N:4]([CH3:18])[CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 962WaterHCID 231533931-benzyl-N,N-dimethylpiperidin-4-amine dihydrochloride

Product 1

HCID 225914404-(Dimethylamino)piperidine dihydrochlorideYield 158.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

After adding 10% palladium-carbon (2.0 g) to a solution of the crude 4-dimethylamino-1-benzylpiperidine dihydrochloride (30.0 g) in 2-propanol (300 ml)-water (300 ml), the mixture was stirred for 22 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered and washed with 2-propanol. The filtrate was then concentrated. The obtained crystals were suspended in ethanol (50 ml). They were then diluted with diethyl ether (50 ml). The crystals were subsequently filtered and washed with methanol (10 ml). They were then subjected to aeration drying to provide the title compound (16.4 g) as colorless crystals.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with 2-propanol
  3. concentrationThe filtrate was then concentrated
  4. additionThey were then diluted with diethyl ether (50 ml)
  5. filtrationThe crystals were subsequently filtered
  6. washwashed with methanol (10 ml)
  7. customdrying

Sources & evidence

ORD record
ord-21c5d9ace9af48b4810dd4b2b2cac66e
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531532B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes