Sodium Hydroxide → 4-Aminomethyl-1-N-Cbz-piperidine

HRID 2217381Notes

Reaction equation

HRID 2217381 reaction equation
FC(F)(F)C([CH:5]([NH2:22])[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1)=O.[OH-].[Na+]>O1CCOCC1>[NH2:22][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131726983HCID 131726983, compound

Product 1

HCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

27.5 g (79.88 mmol) 4-(trifluoroacetyl-aminomethyl)-N(benzyloxycarbonyl)-piperidine are dissolved in 150 ml dioxane and 150 ml 1 N NaOH solution are added. The mixture is stirred for 3 hours at 40° C. and then the solvent is concentrated under vacuum. The residue is collected in water and extracted three times with DCM. The combined DCM phases are dried over Na2SO4 and then the solvent is concentrated under vacuum.

Workup

  1. concentrationthe solvent is concentrated under vacuum
  2. customThe residue is collected in water
  3. extractionextracted three times with DCM
  4. dry with materialThe combined DCM phases are dried over Na2SO4
  5. concentrationthe solvent is concentrated under vacuum

Sources & evidence

ORD record
ord-5f5ca3ded35140819df595a4ac9b532a
Source dataset
uspto-grants-2008_08
Patent number
US07407982B2

Reaction notes

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