Hydrochloric Acid → N-Methyl-1-[2-(2-phenylethyl)phenyl]methanamine

HRID 1288541Notes

Reaction equation

HRID 1288541 reaction equation
Cl.Br[C:3]1[CH:19]=[CH:18][C:6]([CH2:7][CH2:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[CH2:11][NH:12][CH3:13])=[CH:5][CH:4]=1.C(N(CC)CC)C.[H][H].Cl>[Pd].C(O)C>[CH3:13][NH:12][CH2:11][C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[CH2:8][CH2:7][C:6]1[CH:18]=[CH:19][CH:3]=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 21502880HCID 21502880, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21502869N-Methyl-1-[2-(2-phenylethyl)phenyl]methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 2.0 g. (0.00657 mole) of 2-(4-bromo-phenethyl)-N-methylbenzylamine hydrochloride in 200 ml. of absolute ethanol -- 1 ml. of triethylamine is shaken with hydrogen at atmospheric pressure and 25° C. over 400 mg. of 10% palladium on carbon until hydrogen uptake ceases. The catalyst is removed by filtration, the filtrate evaporated to dryness under reduced pressure, and the residue partitioned between aqueous sodium hydroxide and 1:1 ether-benzene. Evaporation of solvents from the washed and dried organic extract leaves the product as the residual oil. The oily base is converted to the hydrochloride salt by treating a solution in absolute ethanol with a slight excess of ethanolic hydrogen chloride. Dilution with absolute ether precipitates the hydrochloride as white crystals, m.p. 204°-206° C. After repeated recrystallizations from absolute ethanol-absolute ether, an analytical sample melts at 205°-206° C.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate evaporated to dryness under reduced pressure
  3. customthe residue partitioned between aqueous sodium hydroxide and 1:1 ether-benzene
  4. customEvaporation of solvents from the
  5. washwashed
  6. extractiondried organic extract
  7. customleaves the product as the residual oil
  8. customDilution with absolute ether precipitates the hydrochloride as white crystals, m.p. 204°-206° C
  9. customrecrystallizations from absolute ethanol-absolute ether

Sources & evidence

ORD record
ord-58968f58d8dd47509bf2825e24ff114c
Source dataset
uspto-grants-1976_10
Patent number
US03988454

Reaction notes

Loading…