Acetophenone → HCID 10491737, compound

HRID 1723798Notes

Reaction equation

HRID 1723798 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)[CH3:15]>C(O)CCC>[CH3:15][C:14]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 67652Tryptamine hydrochloride

Product 1

HCID 10491737HCID 10491737, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1-Methyl-1-phenyl-1,3,4,9-tetrahydrobeta-carboline was prepared by the addition of tryptamine-HCl (500 mg, 2.54 mmol), 1-butanol (12 mL), and acetophenone (1.5 mL, 13 mmol) to a 25 mL flask attached with Dean-Stark Trap. Azeotropic removal of a butanol/H2O mixture was conducted during a vigorous reflux period of 4 hours. The concentrated solution was allowed to stir near reflux for an additional 14 hours. The solution was concentrated under reduced pressure. The residue was taken up into EtOAc (70 mL), washed with sat. NaHCO3 (40 mL×3), washed with H2O (40 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was chromatographed (SiO2 100% DCM to 5% MeOH) to provide 376 mg of 1-methyl-1-phenyl-1,3,4,9-tetrahydrobeta-carboline; 1H NMR (CDCl3) δ 7.74 (1H, br s), 7.54 (1H, d), 7.23-7.32 (6H, m), 7.09-7.21 (2H, m), 3.13 (1H, m), 2.71-2.94 (3H, m), 1.84 (3H, s); 13C NMR (CDCl3) δ 146, 138, 136, 128, 127, 127, 126, 122, 119, 118, 110, 110, 57, 40, 28, 23; TLC (SiO2, 10:1 DCM/MeOH) Rf=0.3; MS (ESI): 263 (MH+).

Workup

  1. customAzeotropic removal of a butanol/H2O mixture
  2. temperaturea vigorous reflux period of 4 hours
  3. temperaturenear reflux for an additional 14 hours
  4. concentrationThe solution was concentrated under reduced pressure
  5. washwashed with sat. NaHCO3 (40 mL×3)
  6. washwashed with H2O (40 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was chromatographed (SiO2 100% DCM to 5% MeOH)

Sources & evidence

ORD record
ord-7c4ba74f54af446fbda8d8f0da577930
Source dataset
uspto-grants-2009_02
Patent number
US07485634B2

Reaction notes

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