[2-(2-Hydroxymethyl-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol → 1-{2-[4-(8-Methoxy-11,13-dihydro-12-oxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-11-yl)-phenoxy]-ethyl}-piperidine

HRID 916864Notes

Reaction equation

HRID 916864 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]=1[CH:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)[OH:22]>Cl.C1COCC1.O>[CH3:20][O:19][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]3[C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[CH2:2][O:22][CH:21]([C:23]4[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:32]5[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]5)=[CH:27][CH:28]=4)[C:10]3=2)[CH:15]=1

Participants

5

Reactant 1

HCID 17987053[2-(2-Hydroxymethyl-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol

Product 1

HCID 589615531-{2-[4-(8-Methoxy-11,13-dihydro-12-oxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-11-yl)-phenoxy]-ethyl}-piperidineYield 64%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add several drops of HCl (5M) to a stirred solution of crude [2-(2-hydroxymethyl-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol in THF (5 mL) and water (0.5 mL). Stir at r.t. for 24 h. Quench with aq. NaHCO3 and dilute with CH2Cl2. Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Purify the crude product by flash chromatography (0-5% (2M NH3/MeOH) in CH2Cl2) to yield 1-{2-[4-(8-methoxy-11,13-dihydro-12-oxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-11-yl)-phenoxy]-ethyl}-piperidine (105 mg, 64%).

Workup

  1. customQuench with aq. NaHCO3
  2. additiondilute with CH2Cl2
  3. washWash the organic phase with water and brine
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude product by flash chromatography (0-5% (2M NH3/MeOH) in CH2Cl2)

Sources & evidence

ORD record
ord-7eab8a486c2f496a96fb06e8310251c6
Source dataset
uspto-grants-2007_09
Patent number
US07271264B2

Reaction notes

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