1-Benzyloxycarbonyl-4-(2-benzyloxyphenyl)piperidine → 2-(Piperidin-4-yl)phenol

HRID 2256056Notes

Reaction equation

HRID 2256056 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23]CC2C=CC=CC=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>O1CCCC1.[Pd]>[OH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 226224391-Benzyloxycarbonyl-4-(2-benzyloxyphenyl)piperidine

Product 1

HCID 107024522-(Piperidin-4-yl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-(2-benzyloxyphenyl)piperidine (1.22 g) in 20 mL of tetrahydrofuran was treated with 10% palladium on carbon catalyst (0.12 g) and hydrogenated at the atmospheric pressure for 16 hours. Upon filtration and evaporation of the filtrate the named product was obtained (0.36 g) as a solid; MS: 178; NMR: 1.8-1.9 (m, 4), 2.7-2.8 (m, 2), 3.0 (m, 1), 3.2 (d, J=12, 2), 5.4 (br, 2), 6.7 (d, J=8, 1), 6.8 (t, J=7, 1), 7.0-7.1 (m, 1), 7.1 (d, J=7, 2).

Workup

  1. filtrationUpon filtration and evaporation of the filtrate the named product
  2. customwas obtained (0.36 g) as a solid

Sources & evidence

ORD record
ord-8c9c456b615440f1a1de87eb92c4b8fb
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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