1-Phenyl-2-(4-pyridinyl)ethanone → HCID 10465342, compound

HRID 1027679Notes

Reaction equation

HRID 1027679 reaction equation
[C:1]1([C:7](=[O:15])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:22].[Na+]>CC(O)C.ClCCl>[CH3:7][OH:15].[NH3:12].[C:1]1([CH:7]([NH2:22])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 2871041-Phenyl-2-(4-pyridinyl)ethanoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 2

HCID 10465342HCID 10465342, compoundYield 78.8%HCID 21705897Ammonia methanolYield 10%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (2) (1.98 g, 10.0 mmol), ammonium acetate (23.2 g, 300 mmol), and sodium cyanoborohydride (4.63 g, 69.9 mmol) in IPA (100 mL) was heated at 80° C. overnight. The mixture was evaporated under reduced pressure to remove IPA. The residue was diluted with water, and basified with NaOH (2M) to pH>7. The aqueous layer was extracted with dichloromethane (3×). The pooled organic layer was removed under vacuum. The residue was purified by chromatography on silica gel (100% ethyl acetate, then 10% saturated ammonia methanol in dichloromethane) to give 1-phenyl-2-(pyridin-4-yl)ethanamine (3) as a clear oil (0.780 g, 3.94 mmol, 39% yield).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customto remove IPA
  3. additionThe residue was diluted with water
  4. extractionThe aqueous layer was extracted with dichloromethane (3×)
  5. customThe pooled organic layer was removed under vacuum
  6. customThe residue was purified by chromatography on silica gel (100% ethyl acetate

Sources & evidence

ORD record
ord-b36371d56be34db2b200d177fcde3e39
Source dataset
uspto-grants-2014_05
Patent number
US08735399B2

Reaction notes

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