Hydrochloric Acid → HCID 12944266, compound

HRID 1277376Notes

Reaction equation

HRID 1277376 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:3].C(OCC)(=O)C.Cl>[Pd].C(OCC)C>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 53794269HCID 53794269, compound

Product 1

HCID 12944266HCID 12944266, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.0 g. of N,N-dimethyl-4-(1,1'-biphenyl-2-yl)-3-butenylamine in 200 ml. of ethyl acetate containing 2.0 g. of five percent palladium oncarbon was stirred for one hour at 25° C. under hydrogen at 40 psi. The reaction mixture then was filtered and the solvent was removed from the filtrate by evaporation to provide an oil. The oil was dissolved in 100 ml. of diethyl ether and stirred while excess hydrogen chloride was added to the solution. The precipitate which formed was collection by filtration and was recrystallized from ethanol and diethyl ether to provide 2.1 g. of N,N-dimethyl-4-(1,1'-biphenyl-2-yl)butylaminum chloride.M.P. 114°-116° C.

Workup

  1. filtrationThe reaction mixture then was filtered
  2. customthe solvent was removed from the filtrate by evaporation
  3. customto provide an oil
  4. dissolutionThe oil was dissolved in 100 ml
  5. additionwas added to the solution
  6. customThe precipitate which formed
  7. customcollection
  8. filtrationby filtration
  9. customwas recrystallized from ethanol and diethyl ether
  10. customto provide 2.1 g

Sources & evidence

ORD record
ord-134cc30c8fbd40b6b0b249c0e127c604
Source dataset
uspto-grants-1981_07
Patent number
US04277471

Reaction notes

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