Sodium Hydroxide → HCID 59449242, compound

HRID 1193360Notes

Reaction equation

HRID 1193360 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C@@H:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][C:15](=O)OCC3C=CC=CC=3)[CH2:9]2)[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:15][NH:14][C@H:10]1[CH2:11][CH2:12][CH2:13][C@@H:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)[CH2:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58235963HCID 58235963, compound

Product 1

HCID 59449242HCID 59449242, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzyl (1S,3R)-3-(4-methylpiperazin-1-yl)cyclohexylcarbamate (2.0 g, 6.0472 mmol, 1.0 eq.) was dissolved in THF (10 ml) and added dropwise at 0° C. to a suspension of LAH (0.345 g, 9.06 mmol, 1.5 eq.) in THF (30 ml). The reaction mixture was then refluxed for 30 minutes. The reaction mixture was subsequently cooled to 0° C., hydrolyzed with 10% NaOH solution (0.35 ml), filtered off and washed with THF (2×50 ml). The filtrate was concentrated under reduced pressure and dried. Yield: 94% (1.2 g, 5.68 mmol)

Workup

  1. temperatureThe reaction mixture was then refluxed for 30 minutes
  2. filtrationfiltered off
  3. washwashed with THF (2×50 ml)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customdried

Sources & evidence

ORD record
ord-29d4d1ba33a047968df5db6ed0cf14e7
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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