HCID 59898559, compound → HCID 59898565, compound

HRID 1362833Notes

Reaction equation

HRID 1362833 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]2[CH2:20][CH2:19][N:18](CC3C=CC=CC=3)[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59898559HCID 59898559, compound

Product 1

HCID 59898565HCID 59898565, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(1-benzyl-piperidin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.51 g) in 20 mL acetic acid was added 0.23 g 10% palladium on carbon, the resulting suspension was shaken under hydrogen (50 psi) in Parr shaker apparatus for 12 hours. The suspension was filtered through a layer of celite and the solvent was removed under vacuum. To the residue was added 10% aq. NaOH and extracted with dichloromethane (2×). The combined organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. The title compound was obtained as clear syrup (1.16 g). ESI MS m/z 284 (M+H+); 1H NMR (400 MHz, CDCl3) δ 4.00 (m, 2H), 3.06 (d, J=10.1 Hz, 2H), 2.74 (m, 4H), 2.57 (t, J=10.1 Hz, 2H), 1.81 (t, J=14.1 Hz, 1H), 1.42 (s, 9H), 1.17 (m, 4H).

Workup

  1. filtrationThe suspension was filtered through a layer of celite and the solvent
  2. customwas removed under vacuum
  3. additionTo the residue was added 10% aq. NaOH
  4. extractionextracted with dichloromethane (2×)
  5. washThe combined organic layers were washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-8cb274644af746f49ac8baca5975e425
Source dataset
uspto-grants-2011_02
Patent number
US07884099B2

Reaction notes

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