Ammonium Chloride → HCID 13677860, compound

HRID 1505650Notes

Reaction equation

HRID 1505650 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C@H:5]1[OH:17])=[N+]=[N-].[Cl-].[NH4+]>CCO.O.C(OCC)(=O)C.N.O.[Zn]>[NH2:1][C@@H:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:6][C@H:5]1[OH:17]

Participants

8

Reactant 2

HCID 25517Ammonium ChlorideHCID 58339729HCID 58339729, compound

Product 1

HCID 13677860HCID 13677860, compoundYield 66.9%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 222AmmoniaSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Procedure

201 mg of trans-4-azido-1-benzylpiperidin-3-ol (0.87 mmol) was dissolved in 3 ml of EtOH-water 3:1. To that solution 77 mg of zinc (12 mmol), 112 mg of ammonium chloride (2.1 mmol) were added and heterogeneous mixture was refluxed for 10 minutes. After cooling down reaction mixture was diluted with 8 mL of ethyl acetate and 0.5 mL of conc. ammonia in water, filtered off. Organic layer washed with brine, dried over sodium sulfate and evaporated. The residue was purified on silica gel column using DCM:MeOH 10:1 as eluent affording 120 mg of trans-4-amino-1-benzylpiperidin-3-ol.

Workup

  1. temperatureheterogeneous mixture was refluxed for 10 minutes
  2. temperatureAfter cooling down
  3. customreaction mixture
  4. filtrationfiltered off
  5. washOrganic layer washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-729425960dda4ad6b2e6ceefe323ef90
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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