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

HRID 1825854ノート

反応式

HRID 1825854 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-0e8859431aa04844a73163ab62f9a641
出典データセット
uspto-grants-2006_05
特許番号
US07049327B2

反応ノート

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