Triethylamine → Tryptamine
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.CCN(CC)CC.[C:21](Cl)(=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[C:21]([NH-:2])(=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[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]=1Participants
Reactant 3
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
These compounds were synthesized by a slightly modified reported procedure (2). Tryptamine hydrochloride salt (0.8 mmol) was dissolved in CH2Cl2 (10 mL) and cooled to 0° C. in an ice bath in a 100 mL round bottom flask. Et3N (3.2 mmol) was added dropwsie to the cold solution followed by addition of n-decanoyl chloride (1.6 mmol). The reaction mixture was stirred for 2 h at room temperature and quenched by addition of water (10 mL) and extracted with CH2Cl2 (3×10 mL). The organic layer was then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with 100% hexanes and 20-30% EtOAc/hexanes to afford N-decanoylamide of tryptamine as an yellow solid (236 mg, 92%). Rf=0.5 (20% EtOAc/hexanes).
Workup
- customThese compounds were synthesized by
- customquenched by addition of water (10 mL)
- extractionextracted with CH2Cl2 (3×10 mL)
- dry with materialThe organic layer was then dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
- washeluting with 100% hexanes and 20-30% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-934020b609604184bb997771c517d722
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073851B2
Reaction notes
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