Ammonium Chloride → 1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]3-hydroxypiperidine

HRID 26061

Reaktionsgleichung

Reaktionsgleichung von HRID 26061
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][C:3]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Mg].[CH2:26]([N:33]1[CH2:38][CH2:37][CH2:36][C:35](=[O:39])[CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>CCOCC.O1CCCC1>[CH2:26]([N:33]1[CH2:38][CH2:37][CH2:36][C:35]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][C:3]=2[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:39])[CH2:34]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 966503-Piperidinone, 1-(phenylmethyl)-HCID 5462224MagnesiumHCID 128821642-(Benzyloxy)-1-bromo-4-(2-methyloctan-2-YL)benzene

Produkt 1

HCID 155715561-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]3-hydroxypiperidineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A solution of 20.0 g. (51.4 mmols) of 1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene in 75 ml. of tetrahydrofuran is slowly added to 2.5 g. (103 mmols) of 70-80 mesh magnesium metal. The resulting mixture is refluxed for 20 minutes and is then cooled to -10° C. A solution of 9.71 g. (51.4 mmols) of N-benzyl-3-piperidone in 25 ml. of tetrahydrofuran is then added at such a rate that the reaction temperature is maintained below 0° C. The reaction mixture is stirred for 30 minutes following completion of addition and is then added to 500 ml. of saturated ammonium chloride and 500 ml. of ether. The ether extract is washed with two 250 ml. portions of sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil is purified via column chromatography on 700 g. of silica gel eluted with 50% ether-cyclohexane to yield 17.1 g. (67%) of the title compound as an oil:

Aufarbeitung

  1. temperatureThe resulting mixture is refluxed for 20 minutes
  2. temperatureis maintained below 0° C
  3. additioncompletion of addition
  4. additionis then added to 500 ml
  5. extractionThe ether extract
  6. washis washed with two 250 ml
  7. dry with materialportions of sodium chloride, dried over magnesium sulfate
  8. customevaporated to an oil
  9. customThe oil is purified via column chromatography on 700 g
  10. washof silica gel eluted with 50% ether-cyclohexane
  11. customto yield 17.1 g

Quellen und Nachweise

ORD-Eintrag
ord-d3b0b30d01ba40e3b9277c3e36967dd2
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04147872

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