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

HRID 1071986Notes

Reaction equation

HRID 1071986 reaction equation
[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

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 110746643,3-Diphenylpropanal

Product 1

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

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-e520eef60b3d4d86b686089b2a7800d7
Source dataset
uspto-grants-2005_06
Patent number
US06908931B2

Reaction notes

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