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

HRID 723348ノート

反応式

HRID 723348 の反応式
[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

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 1927564-Nitro-3-dimethylaminopropiophenoneHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d1c893dcde0c458ba625815b6f249e74
出典データセット
uspto-grants-2006_11
特許番号
US07141561B2

反応ノート

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