Ethanol → HCID 66592967, compound

HRID 1091985Notes

Reaction equation

HRID 1091985 reaction equation
C(O[C:9]1[CH:28]=[CH:27][C:12]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([OH:31])C>[Pd]>[OH:31][C:27]1[CH:28]=[CH:9][CH:10]=[CH:11][C:12]=1[O:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 702EthanolHCID 22458519Tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate

Product 1

HCID 66592967HCID 66592967, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

10% Palladium on carbon (0.75 g, 50% w/w) was added to a solution of tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate (1.5 g) in ethanol (100 mL). The mixture was evacuated and purged with hydrogen twice and then stirred under an atmosphere of hydrogen for 2 hours. The mixture was filtered through celite and the filter pad washed with ethanol. The filtrate was concentrated at reduced pressure to give tert-butyl 4-(hydroxyphenoxy)piperidine-1-carboxylate as a brown solid (1.24 g); NMR Spectrum: (CDCl3) 1.47 (s, 9H), 1.65-1.76 (m, 2H), 1.82-1.93 (m, 2H), 3.23-3.33 (m, 2H), 3.65-3.76 (m, 2H), 4.25-4.34 (m, 1H), 5.07 (s, 1H), 6.70-6.85 (m, 4H).

Workup

  1. customThe mixture was evacuated
  2. custompurged with hydrogen twice
  3. filtrationThe mixture was filtered through celite
  4. washthe filter pad washed with ethanol
  5. concentrationThe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-6bad11c5191149f78961a0fd7b2001f3
Source dataset
uspto-grants-2012_03
Patent number
US08129412B2

Reaction notes

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