Ammonia → HCID 21472906, compound

HRID 1780933Notes

Reaction equation

HRID 1780933 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([CH3:19])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:20].[ClH:21]>C(O)C.[Ni]>[Cl-:21].[CH3:19][CH:17]([NH3+:20])[CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14010323HCID 14010323, compound

Product 1

HCID 21472906HCID 21472906, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 40.0 g of methyl 2-(4-benzyloxyphenyl)ethyl ketone and 160 ml of anhydrous ammonia in 300 ml of ethanol was heated at 75° C. and stirred for two hours. After cooling the reaction mixture to room temperature, 4.0 g of Raney nickel was added in one portion, and the reaction mixture then was stirred at 25° C. for twelve hours under a hydrogen atmosphere at 300 psi. The reaction mixture next was filtered and the filtrate was concentrated by evaporation of the solvent under reduced pressure to provide an oil. The oil was dissolved in 120 ml of 3N hydrochloric acid, from which the product as a hydrochloride salt precipitated. The salt so formed was collected by filtration and recrystallized from methanol and toluene to provide 36.2 g of dl-1-methyl-3-(4-benzyloxyphenyl)propylaminium chloride. M.P. 195°-197.5° C.

Workup

  1. stirringthe reaction mixture then was stirred at 25° C. for twelve hours under a hydrogen atmosphere at 300 psi
  2. filtrationThe reaction mixture next was filtered
  3. concentrationthe filtrate was concentrated by evaporation of the solvent under reduced pressure
  4. customto provide an oil
  5. customprecipitated
  6. customThe salt so formed
  7. filtrationwas collected by filtration
  8. customrecrystallized from methanol and toluene

Sources & evidence

ORD record
ord-f04b1eaf04fb4dce92f8799d2cdb1db8
Source dataset
uspto-grants-1997_05
Patent number
US05631298

Reaction notes

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