Benzyl({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)carbamate → 2H-Pyran-4-ol, 4-[[4-(aminomethyl)-1-piperidinyl]methyl]tetrahydro-

HRID 502900Notes

Reaction equation

HRID 502900 reaction equation
C(OC(=O)[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2([OH:25])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:14][CH2:13]1)C1C=CC=CC=1>[Pd].CO>[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2([OH:25])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 59255048Benzyl({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)carbamate

Product 1

HCID 592550572H-Pyran-4-ol, 4-[[4-(aminomethyl)-1-piperidinyl]methyl]tetrahydro-Yield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)carbamate (5.60 g, 15.5 mmol, step 1) and palladium on activated carbon (10 wt. %, 1.20 g) in methanol (250 mL) was hydrogenated at room temperature for 20 h. Then, the mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to give 3.30 g (94%) of the title compound as slightly yellow oil.

Workup

  1. filtrationThen, the mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-89608e73f7314718b732bf492f5a006a
Source dataset
uspto-grants-2010_08
Patent number
US07776885B2

Reaction notes

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