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 1830514Notes

Reaction equation

HRID 1830514 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-711b928eb038474b9c0e404465847c9d
Source dataset
uspto-grants-2006_06
Patent number
US07067510B2

Reaction notes

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