Ammonia → HCID 15965878, compound

HRID 2365522Notes

Reaction equation

HRID 2365522 reaction equation
[Cl-].[NH4+:2].[NH3:3].[CH2:4]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C-:18]#N.[Na+]>O>[NH2:2][CH2:18][C:14]1([NH2:3])[CH2:15][CH2:16][N:11]([CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium Chloride

Product 1

HCID 15965878HCID 15965878, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of ammonium chloride (1.73 g, 32.3 mmol) in water (20 ml) is added a 30% ammonia solution (2 ml) followed by 1-benzyl-4-piperidone. After 20 minutes sodium cyanide (1.47 g, 30 mmol) is added portionwise over 15 minutes. After stirring for one hour, water (50 ml) is added and the products are extracted with DCM (3×50 ml), dried (MgSO4) filtered and concentrated in vacuo. Purification by chromatography on silica eluting with 50-100% EtOAc in iso-hexane affords 4-Aminomethyl-1-benzyl-piperidine-4-ylamine; [M+H]+ 216

Workup

  1. extractionthe products are extracted with DCM (3×50 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica eluting with 50-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-0dc61bdd56504ca2bd60883348230199
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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