Homoveratrylamine → 1-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1071986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071986
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH2:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]>C(O)=O>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH:9]2[C:22]3[C:21](=[CH:20][C:19]([O:18][CH3:17])=[C:24]([O:25][CH3:26])[CH:23]=3)[CH2:27][CH2:28][NH:29]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 8421HomoveratrylamineHCID 110746643,3-Diphenylpropanal

Produkt 1

HCID 223910171-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A solution of 3,3-diphenylpropionaldehyde (19.25 g, 91.54 mmoles) and 2-(3,4-dimethoxyphenyl)ethylamine (16.59 g, 1 equiv.) in 90% formic acid 125 mL) was heated at 95° C. for 16 hours. Upon cooling to room temperature, the solvent was removed on the rotary evaporator, and the residue was partitioned between ethyl acetate and 1M sodium hydroxide. The organic phase was washed with 1M sodium hydroxide and brine, dried over sodium sulfate, and evaporated to give a thick gum. The product was purified by flash chromatography on silica gel, eluting with 20:1 ethyl acetate/methanol, to give a thick gum that solidified upon standing (17.01 g, 50%). 1H-NMR (CDCl3) δ 2.42 (m, 1H), 2.53 (m, 1H), 2.67 (m, 2H), 2.98 (m, 1H), 3.18 (m, 1H), 3.77 (ABq, 1H), 3.84 and 3.88 (s, each 3H), 4.48 (ABq, 1H), 6.46 and 6.57 (s, each 1H), 7.32 (m, 10 H). Mass spec. 374.2 (MH)+.

Aufarbeitung

  1. customthe solvent was removed on the rotary evaporator
  2. customthe residue was partitioned between ethyl acetate and 1M sodium hydroxide
  3. washThe organic phase was washed with 1M sodium hydroxide and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give a thick gum
  7. customThe product was purified by flash chromatography on silica gel
  8. washeluting with 20:1 ethyl acetate/methanol
  9. customto give a thick gum that

Quellen und Nachweise

ORD-Eintrag
ord-e520eef60b3d4d86b686089b2a7800d7
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908931B2

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