Triethylamine → Amitriptyline

HRID 1654438

Reaktionsgleichung

Reaktionsgleichung von HRID 1654438
[CH:1]1[C:6](C(O)=O)=[CH:5][C:4]([C:10]2C3C=CC(O)=CC=3OC3[C:11]=2[CH:12]=[CH:13][C:14]([CH:16]=3)=O)=[C:3](C(O)=O)[CH:2]=1.ON1[C:34](=O)[CH2:33][CH2:32][C:31]1=O.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:52]([N:54]([CH2:57]C)[CH2:55][CH3:56])C>CN(C=O)C>[CH3:57][N:54]([CH2:55][CH2:56][CH:31]=[C:32]1[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:16]=[CH:34][C:33]1=2)[CH3:52]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2725051ST51005980

Produkt 1

HCID 2160Amitriptyline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

6-Carboxyfluorescein (1.00 g, 2.66 mmol) was dissolved in 8 mL DMF, 306 mg (2.66 mmol) of N-hydroxysuccinimide (HOSu) was added, 549 mg (2.66 mmol) of 1,3-dicyclohexylcarbodiimide (DCC) was added, and the reaction stirred for 17 hours, under N2, in the dark. The reaction was then vacuum filtered, filtrate combined with 784 mg (2.65 mmol) of 2-aminoimipramine (26c), 0.56 mL (4.0 mmol) of triethylamine, and 4.0 mL DMF, and reaction allowed to stir 4 days under N2, in the dark. Reaction solvents were removed in vacuo and residue purified on reverse phase C18 preparative (1 mm) TLC plates, eluting with H2O/THF/HOAc (40/60/0.4) followed by preparative HPLC on a Waters mbondapak C18 column (19 mm×150 mm), eluting with H2O/THF/HOAc (35/65/0.4) at a flow rate of 7.0 mL/minute to yield 410 mg (24%) of the desired tracer (27) as an orange powder; mass spec (FAB) (M+H)+ 654.

Aufarbeitung

  1. filtrationvacuum filtered
  2. stirringto stir 4 days under N2, in the dark
  3. customReaction solvents
  4. customwere removed in vacuo and residue
  5. custompurified on reverse phase C18 preparative (1 mm) TLC plates
  6. washeluting with H2O/THF/HOAc (40/60/0.4)
  7. washeluting with H2O/THF/HOAc (35/65/0.4) at a flow rate of 7.0 mL/minute

Quellen und Nachweise

ORD-Eintrag
ord-f2f080c2bc3648e496e1ef9e2f5f9d09
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05407835

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