6-(2-Hydroxy-benzyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol → 13-[4-(2-Piperidin-1-yl-ethoxy)-phenyl]-7,13-dihydro-12-oxa-benzo[4,5]cyclohepta[1,2-a]naphthalen-3-ol

HRID 2223682Notes

Reaction equation

HRID 2223682 reaction equation
O[C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][C:5]1[C:6]([CH:16]([OH:32])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:19][CH:18]=2)=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([OH:15])[CH:9]=[CH:8]2>Cl.C(Cl)Cl>[N:26]1([CH2:25][CH2:24][O:23][C:20]2[CH:21]=[CH:22][C:17]([CH:16]3[C:6]4[C:7]5[CH:8]=[CH:9][C:10]([OH:15])=[CH:11][C:12]=5[CH:13]=[CH:14][C:5]=4[CH2:4][C:3]4[CH:2]=[CH:36][CH:35]=[CH:34][C:33]=4[O:32]3)=[CH:18][CH:19]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 1

HCID 100509856-(2-Hydroxy-benzyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol

Product 1

HCID 998196313-[4-(2-Piperidin-1-yl-ethoxy)-phenyl]-7,13-dihydro-12-oxa-benzo[4,5]cyclohepta[1,2-a]naphthalen-3-olYield 56%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 6-(2-hydroxy-benzyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol (80 mg, 0.17 mmol) in HCl solution (20% 1M aq. HCl in THF). Stir at r.t. for 2 h and warm gently for 10 min. Dilute with CH2Cl2, wash with sat. NaHCO3, water and brine, dry over MgSO4, filter and concentrate. Purify the crude product by flash chromatography (0-5% (2M NH3 in MeOH)/CH2Cl2) to afford 13-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-7,13-dihydro-12-oxa-benzo[4,5]cyclohepta[1,2-a]naphthalen-3-ol (43 mg, 56%).

Workup

  1. temperaturewarm gently for 10 min
  2. washwash with sat. NaHCO3, water and brine
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude product by flash chromatography (0-5% (2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-ffeb34bdd157465983a2f47ef8acf1ba
Source dataset
uspto-grants-2008_05
Patent number
US07375229B2

Reaction notes

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