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

HRID 1825854노트

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HRID 1825854 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-0e8859431aa04844a73163ab62f9a641
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049327B2

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