Sodium Hydroxide → HCID 59597674, compound

HRID 1193329Notes

Reaction equation

HRID 1193329 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=O)OC(C)(C)C)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C1COCC1.[OH-].[Na+]>C1COCC1>[CH3:15][NH:14][CH2:13][CH:10]1[CH2:11][CH2:12][N:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 20801237tert-Butyl (1-(pyridin-4-yl)piperidin-4-yl)methylcarbamateHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 59597674HCID 59597674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of tert-butyl (1-(pyridin-4-yl)piperidin-4-yl)methylcarbamate (180 mg, 0.618 mmol, 1 eq) in THF (4 ml) was added dropwise at 0° C. to a suspension of LAH (188 mg, 4.94 mmol, 8 eq) in THF (4 ml) and heated for 16 h at boiling temperature. The reaction mixture was hydrolyzed with H2O:THF (9:1, 2 ml) and 10% NaOH solution (0.4 ml) at 0° C., diluted with THF (25 ml) and stirred for 1 h at RT. The reaction mixture was filtered over Celite and the filtrate was concentrated under reduced pressure. The resulting amine was used in the following stage without being purified further. Yield: 150 mg.

Workup

  1. temperatureheated for 16 h
  2. filtrationThe reaction mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customwithout being purified further

Sources & evidence

ORD record
ord-75ed86f6b82b416aa6c97daaa367e55f
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…