Phenol → 3-Dimethylaminomethyl-4-(3-hydroxy-phenyl)-1-(1-phenyl-cyclohexyl)-piperidin-4-ol Dihydrochloride

HRID 1825854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825854
COC.C1(O)C=CC=CC=1.[ClH:11].Cl.[CH3:13][N:14]([CH2:16][CH:17]1[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30]C)[CH:25]=2)([OH:23])[CH2:21][CH2:20][N:19]([C:32]2([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:18]1)[CH3:15].[H-].C([Al+]CCCC)CCC>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C>[ClH:11].[ClH:11].[CH3:15][N:14]([CH2:16][CH:17]1[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)([OH:23])[CH2:21][CH2:20][N:19]([C:32]2([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH2:18]1)[CH3:13]

Komponenten

8

Edukt 4

HCID 996PhenolHCID 8254Dimethyl EtherHCID 103003283-Dimethylaminomethyl-4-(3-methoxyphenyl)-1-(1-phenyl-cyclohexyl)-piperidin-4-ol DihydrochlorideHCID 21879971Dibutylaluminium hydride

Produkt 1

HCID 101843763-Dimethylaminomethyl-4-(3-hydroxy-phenyl)-1-(1-phenyl-cyclohexyl)-piperidin-4-ol Dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The synthesis instructions are described analogously to Example 6, except for the last step. The methyl ether was then cleaved into the phenol. To that end, 0.5 g (1.2 mmol.) of the free base of compound (6) was dissolved in 5 ml of toluene, and 10 ml of dibutylaluminium hydride solution (1.5 M in toluene) were added at 0° C. and under a nitrogen atmosphere. After 12 hours' stirring, the batch was hydrolysed with 5 ml of ethyl acetate and 5 ml of ethanol, the solvent was removed in vacuo, the residue was dissolved in methyl ethyl ketone, and 1.0 ml of trimethylsilyl chloride was added thereto. The yield of (11) was 71 mg (0.15 mmol., 12%). The compound melted between 245 and 248° C.

Aufarbeitung

  1. customThe synthesis instructions
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in methyl ethyl ketone
  4. addition1.0 ml of trimethylsilyl chloride was added
  5. custommelted between 245 and 248° C.

Quellen und Nachweise

ORD-Eintrag
ord-0e8859431aa04844a73163ab62f9a641
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049327B2

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