Methanol → HCID 68952808, compound

HRID 929746Notes

Reaction equation

HRID 929746 reaction equation
C[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH:15]2[CH2:16][C:17]([CH2:19][CH:12]1[CH2:13][CH2:14]2)=O.[CH3:20]O>C1(C)C=CC=CC=1.ClCCl>[CH3:20][CH:19]1[C@H:12]2[N:11]([CH3:10])[C@H:15]([CH2:14][CH2:13]2)[C:16](=[N:7][CH2:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:9][CH:8]=2)[CH2:17]1

Participants

6

Reactant 3

HCID 887MethanolHCID 660354-MethylbenzylamineHCID 79038Npc164516

Product 1

HCID 68952808HCID 68952808, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methylbenzylamine (1.21 g, 10 mmol) and Tropinone (1.39 g, 10 mmol) were placed in 100 ml flask and dissolved in 50 ml toluene. Mixture was heated to reflux for 3 hrs and water was removed using a Dean/Stark water-separator. Crude product was concentrated on Rotavapor (40° C.) giving 47AKU-38. TLC (10% methanol in dichloromethane): Rf=0.3. 1H-NMR (400 MHz, CDCl3, isomers): 7.20-7.09 (4H, m); 4.47 (1H, m); 3.81 (1H, s); 3.42 (1H, m); 3.31 (1H, m); 2.77-2.56 (2H, m); 2.47 and 2.41 (3H, 2s); 2.33 and 2.31 (3H, 2s); 2.27-1.97 (4H, m); 1.69-1.54 (2H, m).

Workup

  1. temperatureMixture was heated
  2. temperatureto reflux for 3 hrs
  3. customwater was removed
  4. concentrationCrude product was concentrated on Rotavapor (40° C.)
  5. customgiving 47AKU-38

Sources & evidence

ORD record
ord-306abd5219644a2fb335b01da9d2179e
Source dataset
uspto-grants-2016_03
Patent number
US09296694B2

Reaction notes

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