Tert-butyl 4-[2-[4-(1-(benzyloxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate → Tert-butyl 4-[2-[4-(piperidin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate

HRID 2381092Notes

Reaction equation

HRID 2381092 reaction equation
C(OC([N:11]1[CH2:16][CH:15]=[C:14]([C:17]2[CH:38]=[CH:37][C:20]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>[Pd].CO>[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:38]=[CH:37][C:20]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:26][CH2:25]3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 66788330Tert-butyl 4-[2-[4-(1-(benzyloxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate

Product 1

HCID 66788225Tert-butyl 4-[2-[4-(piperidin-4-yl)phenoxy]ethyl]piperazine-1-carboxylateYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-[2-[4-(1-(benzyloxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate (66% pure by weight) (34.62 g, 43.80 mmol) and 5% palladium on carbon (50% wet) (4.47 g, 1.05 mmol) in MeOH (250 mL) were stirred under an atmosphere of hydrogen at 5 bar and 60° C. for 4 hours. The catalyst was removed by filtration and the solvents evaporated to give crude product. The crude product was purified by flash silica chromatography, eluting with 60% EtOAc in isohexane then 15% 2M ammonia/MeOH in DCM. Pure fractions were evaporated to dryness to afford tert-butyl 4-[2-[4-(piperidin-4-yl)phenoxy]ethyl]piperazine-1-carboxylate (15.42 g, 90%) as a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents evaporated
  3. customto give crude product
  4. customThe crude product was purified by flash silica chromatography
  5. washeluting with 60% EtOAc in isohexane
  6. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-59321207f50a42e6bb97ef341b4e98a8
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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