Hydrochloric Acid → N-[3-(4-Aminophenyl)propyl]-N,N-dimethylamine

HRID 723348Notes

Reaction equation

HRID 723348 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)=O.Cl.[H][H]>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1927564-Nitro-3-dimethylaminopropiophenoneHCID 178418361HCID 178418361, compound

Product 1

HCID 2761029N-[3-(4-Aminophenyl)propyl]-N,N-dimethylamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3-dimethylamino-1-(4-nitrophenyl)propan-1-one (hydrochloride, 0.25 g) in glacial acetic acid (10 ml) was adjusted to pH 1 with concentrated hydrochloric acid and, under nitrogen, palladium(II) hydroxide (20% on carbon, 0.1 g) was added. The nitrogen atmosphere was replaced by hydrogen, and the suspension was shaken for 6 hours. The catalyst was filtered off and the filtrate was concentrated. The residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The aqueous phase was adjusted to pH>12 with sodium hydroxide solution and extracted with ethyl acetate. The combined organic phases were dried and concentrated. The product with the molecular weight of 178.28 (C11H18N2); MS (ESI): 179 ([M+H]+), was obtained in this way.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  4. extractionextracted with ethyl acetate
  5. customThe combined organic phases were dried
  6. concentrationconcentrated
  7. customMS (ESI): 179 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-d1c893dcde0c458ba625815b6f249e74
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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