Succinic anhydride → N-Butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-succinamic Acid

HRID 1708622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708622
[CH2:1]([NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]([CH3:22])([CH3:21])[CH2:7]1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:30]1(=[O:36])[O:35][C:33](=[O:34])[CH2:32][CH2:31]1>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:5]([CH:6]1[CH2:7][C:8]([CH3:21])([CH3:22])[N:9]([O:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[C:10]([CH3:13])([CH3:12])[CH2:11]1)[C:30](=[O:36])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 211821294-Butylamino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

Produkt 1

HCID 23372132N-Butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-succinamic AcidAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 10.2 grams (33 mmol) of 4-n-butylamino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine (prepared in Example 8), 3.3 grams (33 mmol) of triethylamine, and 30 ml of tetrahydrofuran is added to a solution of 3.0 grams (30 mmol) of succinic anhydride in 20 ml of tetrahydrofuran over a 5-minute period. The reaction mixture is stirred for six hours and then diluted with ethyl acetate (200 ml). The organic solution is washed with 1N hydrochloric acid (2×50 ml), washed with water (50 ml), washed with saturated sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give an oil which crystallizes on standing. Recrystallization from heptane affords 5.6 grams (46% yield) of the title compound as a white solid melting at 110°-113° C.

Aufarbeitung

  1. washThe organic solution is washed with 1N hydrochloric acid (2×50 ml)
  2. washwashed with water (50 ml)
  3. washwashed with saturated sodium chloride solution (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil which
  7. customcrystallizes
  8. customRecrystallization from heptane

Quellen und Nachweise

ORD-Eintrag
ord-6854c0adc7a946f796c4ea0edc47c52f
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05359069

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