Diisopropylethylamine → HCID 178484845, Verbindung

HRID 1063621

Reaktionsgleichung

Reaktionsgleichung von HRID 1063621
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.C(N(CC)C(C)C)(C)C.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[OH:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([N:2]([CH3:1])[S:27]([C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:31])[F:32])=[CH:26][CH:25]=2)(=[O:29])=[O:28])[CH2:4][CH2:5]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 178484843HCID 178484843, Verbindung

Produkt 1

HCID 178484845HCID 178484845, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 3 g (23.2 mmol) of trans-4-methylamino-cyclohexanol in 120 mL of CH2Cl2 were added 4.2 mL (24.4 mmol, 1.05 eq) of N,N-diisopropylethylamine followed by 5.96 g (24.4 mmol, 1.05 eq) of 4-(trifluoromethyl)-benzenesulfonyl chloride in 50 mL of CH2Cl2. The mixture was stirred at RT over night and the organic phase was extracted with 1M KHSO4, followed by 5% NaHCO3. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-hexane:EtOAc 1:1 as eluent yielded 6.0 g (77%) of trans-N-(4-hydroxy-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide as off-white solid, MS: 338 (MH+).

Aufarbeitung

  1. extractionthe organic phase was extracted with 1M KHSO4
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ef16aeb14d6847a4afcdd8483c2f5d7a
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06965048B2

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