Triethylamine → N-(3,4-Dimethoxybenzenesulphonyl)-1,2,3,4-tetrahydroquinoline

HRID 2142

Reaktionsgleichung

Reaktionsgleichung von HRID 2142
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([S:21](Cl)(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].C(N(CC)CC)C>ClCCl>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([S:21]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)(=[O:22])=[O:23])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 694601,2,3,4-TetrahydroquinolineHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

Produkt 1

HCID 667562N-(3,4-Dimethoxybenzenesulphonyl)-1,2,3,4-tetrahydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1,2,3,4-Tetrahydroquinoline (0.29 ml) was added to a suspension of 3,4-dimethoxybenzene sulphonyl chloride (0.50 g) in dichloromethane (15 ml) at room temperature. Triethylamine (0.44 ml) was added and the resulting mixture stirred for 24 hours at room temperature. The reaction mixture was then diluted with dichloromethane (20 ml) and washed successively with saturated aqueous sodium hydrogen carbonate solution (10 ml), 2N hydrochloric acid (10 ml) and saturated aqueous sodium chloride solution (10 ml). Drying over magnesium sulphate and concentration in vacuo provided a yellow oil. Purification by column chromatography eluting with 30% ethyl acetate in hexane provided the title compound as a colourless oil (0.60 g) which solidified on standing.

Aufarbeitung

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate solution (10 ml), 2N hydrochloric acid (10 ml) and saturated aqueous sodium chloride solution (10 ml)
  2. dry with materialDrying over magnesium sulphate and concentration in vacuo
  3. customprovided a yellow oil
  4. customPurification by column chromatography
  5. washeluting with 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-80b4d3c6a338477cbce6e4a97e49acd8
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728712

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