Tryptamine → HCID 44237930, compound

HRID 2066959Notes

Reaction equation

HRID 2066959 reaction equation
[CH2:1]([CH:8]1[CH2:13][C:12]([N:20]([CH3:22])[CH3:21])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][CH2:25][CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>CO>[CH2:1]([CH:8]1[C:9]2([C:28]3[NH:29][C:30]4[C:35]([C:27]=3[CH2:26][CH2:25][NH:24]2)=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([N:20]([CH3:22])[CH3:21])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67409230HCID 67409230, compound

Product 1

HCID 44237930HCID 44237930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-2-benzyl-4-dimethylamino-4-phenylcyclohexanone (307 mg, 1 mmol) together with tryptamine (160 mg, 1 mmol) was dissolved in methanol and stirred at RT for 24 h. The solvent was then removed in a vacuum and the residue dissolved in 1,2-dichloroethane (20 ml). The mixture was mixed with trifluoroacetic acid (1.7 ml, 22.8 mmol) and stirred for 24 h at RT. For work up the reaction mixture was mixed with 2N NaOH (20 ml) and stirred for 20 min. The organic phase was separated and the aqueous phase extracted with dichloromethane (4×20 ml). The combined organic phases were dried with MgSO4. The solvent was then concentrated by evaporation in a vacuum. One of the possible diastereoisomers was isolated from the residue obtained (260 mg) by means of chromatographic purification [silica gel 60 G (10 g); ethyl acetate/ethanol 1:1 (80 ml), methanol (60 ml)].

Workup

  1. customThe solvent was then removed in a vacuum
  2. dissolutionthe residue dissolved in 1,2-dichloroethane (20 ml)
  3. stirringstirred for 24 h at RT
  4. stirringstirred for 20 min
  5. customThe organic phase was separated
  6. extractionthe aqueous phase extracted with dichloromethane (4×20 ml)
  7. dry with materialThe combined organic phases were dried with MgSO4
  8. concentrationThe solvent was then concentrated by evaporation in a vacuum
  9. customOne of the possible diastereoisomers was isolated from the residue
  10. customobtained (260 mg)
  11. customby means of chromatographic purification [silica gel 60 G (10 g); ethyl acetate/ethanol 1:1 (80 ml), methanol (60 ml)]

Sources & evidence

ORD record
ord-3c7eb237678c481ca4f4fe97838a8fc3
Source dataset
uspto-grants-2012_10
Patent number
US08293758B2

Reaction notes

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