3-Amino-1-propanol → 3-[3-(Anthracen-9-ylmethyl-ethyl-amino)-propylamino]-propan-1-ol

HRID 12995

Reaktionsgleichung

Reaktionsgleichung von HRID 12995
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][N:16]([CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19]OS(C)(=O)=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31]>C(#N)C>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][N:16]([CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19][NH:27][CH2:28][CH2:29][CH2:30][OH:31])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 90863-Amino-1-propanolHCID 86615041Methanesulfonic acid 3-(anthracen-9-ylmethyl-ethyl-amino)-propyl ester

Produkt 1

HCID 247441943-[3-(Anthracen-9-ylmethyl-ethyl-amino)-propylamino]-propan-1-olAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

The mesylate 17 (384 mg, 1.04 mmol) and 3-amino-propanol (392 mg, 5.25 mmol) were dissolved in acetonitrile (20 mL). The mixture was then stirred at 75° C. under a N2 atmosphere overnight. After the confirmation of the disappearance of the mesylate by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 18 as a light yellow oil. Yield 65%; Rf=0.35 (1:6:83 NH4OH:MeOH:CH2Cl2); 1H NMR (CDCl3) δ 8.32 (d, 2H), 8.23 (s, 1H), 7.83 (d, 2H), 7.37 (m, 2H), 7.30 (m, 2H), 4.28 (s, 2H), 3.48 (t, 2H), 2.56 (q, 2H), 2.30 (t, 2H), 2.12 (t, 2H), 2.06 (t, 2H), 1.36 (q, 2H), 1.21 (q, 2H), 1.09 (t, 3H); 13C NMR (CDCl3) δ 131.3, 131.2, 130.5, 129.3, 129.0, 127.3, 125.5, 125.3, 124.8, 124.8, 63.8, 50.8, 50.5, 49.5, 48.3, 47.7, 30.5, 26.6, 11.7. HRMS (FAB) m/z calcd. for C23H30N2O (M+H)+ 351.2431; found 351.2430.

Aufarbeitung

  1. concentrationAfter the confirmation of the disappearance of the mesylate by TLC, the solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. washwashed three times with aqueous sodium carbonate
  4. customThe organic layer was separated
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f55185bace004fc98710a0598b4931b8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728041B2

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