Ammonia → HCID 15965878, compound

HRID 2281595Notes

Reaction equation

HRID 2281595 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-b2a5f1862aa8496e902da410a92a504a
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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