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 1809346Notes

Reaction equation

HRID 1809346 reaction equation
[OH:1][C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16]C(=O)OCC3C=CC=CC=3)[CH2:11][CH2:10]2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1>[Pd].CO>[NH2:16][CH2:15][CH:12]1[CH2:13][CH2:14][N:9]([CH2:8][C:2]2([OH:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)[CH2:10][CH2:11]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 as prepared in 1(1) (5.60 g, 15.5 mmol) 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-95be4138b2db4defbb7d504ed28b4e90
Source dataset
uspto-grants-2013_01
Patent number
US08362038B2

Reaction notes

Loading…