2,4-Dimethoxybenzylamine → HCID 16730729, compound

HRID 507333Notes

Reaction equation

HRID 507333 reaction equation
[O:1]1[CH2:18][C@@H:2]1[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH3:19][O:20][C:21]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:22]=1[CH2:23][NH2:24]>CCOC(C)=O.CC(O)C>[CH:8]1[C:9]2[NH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[C:5]([O:4][CH2:3][C@H:2]([OH:1])[CH2:18][NH:24][CH2:23][C:22]2[CH:25]=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:21]=2[O:20][CH3:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 133708844-{[(2R)-Oxiran-2-yl]methoxy}-9H-carbazole

Product 1

HCID 16730729HCID 16730729, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 22055037Isopropanol ethyl acetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (R)-(−)-4-(2,3-Epoxypropoxy)-carbazole (7 g, 0.029 mole) in EtOAc/IPA (40/80 mL) was added 2,4-dimethoxybenzylamine (8.7 mL, 0.058 mole) and the reaction mixture was slowly heated to 80-90° C. and then refluxed for 5 hours. Subsequently the reaction mixture was concentrated to half its volume, and cooled to room temperature to give a colorless solid. The solid was filtered, re-dissolved in EtOAc (60 mL) by refluxing, concentrated to 40 mL and the colorless precipitate formed on cooling to room temperature, was filtered and dried. Recrystallization of the residue obtained from the filtrate was repeated until maximum amount of the solid was recovered. The combined solid was triturated with diethylether by stirring for 6 hours, followed by filtration to afford 5.5 g (46% yield) of the desired compound as a colorless solid with m.p: 152-153° C. 1H NMR (400 MHz, CDCl3): δ 2.17 (s 1H), 2.86-2.92 (m, 1H), 2.99-3.02 (m, 1H), 3.74-3.86 (m, 8H), 4.18-4.32 (m, 3H), 6.38-6.44 (m, 2H), 6.67 (d, 1H, J=8.0 Hz), 7.04 (d, 1H, J=8.0 Hz), 7.12 (d, 1H, J=8.0 Hz), 7.18-7.41 (m, 4H), 8.09 (s, 1H), 8.21 (d, 1H, J=8.0 Hz). MS m/z: 407.1 (M+1). Chiral purity: 99.99%

Workup

  1. temperaturerefluxed for 5 hours
  2. concentrationSubsequently the reaction mixture was concentrated to half its volume
  3. temperaturecooled to room temperature
  4. customto give a colorless solid
  5. filtrationThe solid was filtered
  6. dissolutionre-dissolved in EtOAc (60 mL)
  7. temperatureby refluxing
  8. concentrationconcentrated to 40 mL
  9. customthe colorless precipitate formed
  10. temperatureon cooling to room temperature
  11. filtrationwas filtered
  12. customdried
  13. customRecrystallization of the residue
  14. customobtained from the filtrate
  15. customwas recovered
  16. customThe combined solid was triturated with diethylether
  17. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-112aebe74f3c40288544ee1093a19e83
Source dataset
uspto-grants-2010_08
Patent number
US07786142B2

Reaction notes

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