[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 916864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916864
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

Komponenten

5

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-7eab8a486c2f496a96fb06e8310251c6
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271264B2

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