Tryptamine → HCID 58101313, compound

HRID 237320Notes

Reaction equation

HRID 237320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][CH2:24][NH2:25])=[CH:15]1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:15]4[NH:14][C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16]=4[CH2:23][CH2:24][NH:25]3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 99423881-(4-Chlorophenyl)cyclobutanecarbaldehyde

Product 1

HCID 58101313HCID 58101313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Chlorophenyl)cyclobutanecarbaldehyde (30 mg, 0.154 mmol) and 2-(1H-indol-3-yl)ethanamine (27.7 mg, 0.17 mmol) were dissolved in dichloromethane (3 mL). Trifluoroacetic acid (88 mg, 0.771 mmol) were added at 0° C. and the reaction mixture was stirred at room temperature over night. The 5% NaHCO3 solution was added. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed successively with 5% NaHCO3 solution and saturated sodium chloride solution, dried (MgSO4) and concentrated in vacuo. Yield: 36 mg (oil, 0.107 mmol, 69%).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane
  2. washThe combined organic layers were washed successively with 5% NaHCO3 solution and saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55fb936d2ac0410eb14a7093c0923c90
Source dataset
uspto-grants-2014_02
Patent number
US08642587B2

Reaction notes

Loading…