Hydrochloric Acid → 2-Propanol, 1-[(2-amino-1,1-dimethylethyl)amino]-3-(2-methylphenoxy)-

HRID 745508Notes

Reaction equation

HRID 745508 reaction equation
Cl.[CH3:2][C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[O:5][CH2:6][CH:7]([OH:29])[CH2:8][NH:9][C:10]([CH3:28])([CH3:27])[CH2:11][N:12](CC1C=CC=CC=1)CC1C=CC=CC=1>C(O)C.[C].[Pd]>[CH3:2][C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[O:5][CH2:6][CH:7]([OH:29])[CH2:8][NH:9][C:10]([CH3:28])([CH3:27])[CH2:11][NH2:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 537951651-(2-Methylphenoxy)-3-(1,1-dimethyl-2-dibenzylaminoethylamino)-2-propanol

Product 1

HCID 100607882-Propanol, 1-[(2-amino-1,1-dimethylethyl)amino]-3-(2-methylphenoxy)-Yield 90.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Concentrated hydrochloric acid (1.4 ml) and 5% palladium carbon was added to a solution of 3 g of 1-(2-methylphenoxy)-3-(1,1-dimethyl-2-dibenzylaminoethylamino)-2-propanol in 10 ml of ethanol, and the mixture was hydrogenated at room temperature for 24 hours. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was dissolved in water, made alkaline with potassium carbonate, then extracted with chloroform, and dried over anhydrous magnesium sulfate. 1.585 g of 1-(2-methylphenoxy)-3-(1,1-dimethyl-2-aminoethylamino)-2-propanol was obtained as a colorless oil.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-1c53379146c742659cfdfcc3488143c6
Source dataset
uspto-grants-1986_07
Patent number
US04599333

Reaction notes

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