Tryptamine → HCID 66782732, compound
Reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C1COCC1.C(N(CC)CC)C.[CH:25]1([S:30](Cl)(=[O:32])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26]1>C(Cl)(Cl)Cl.CO.C(OCC)(=O)C>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][NH:1][S:30]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)(=[O:32])=[O:31])=[CH:5]1Participants
Procedure
Tryptamine (950 mg, 5.93 mmol) was initially introduced into abs. THF (30 ml), and triethylamine (0.82 ml, 5.93 mmol) was added at RT. Cyclopentanesulfonyl chloride (1.00 g, 5.93 mmol) was then swiftly added dropwise at RT and the mixture was stirred at RT for 1 d. A subsequent TLC in chloroform/methanol 20:1 showed only small amounts still of tryptamine. The mixture was concentrated i. vac., the residue obtained was taken up in ethyl acetate (20 ml) and the mixture was washed with saturated NaHCO3 solution (2×20 ml). A precipitate precipitated out of the solution, this was filtered off with suction, but according to TLC it was not the product. The organic phase was washed with saturated NaCl solution (2×20 ml), dried over Na2SO4 and concentrated i. vac.
Workup
- concentrationThe mixture was concentrated i
- custom, the residue obtained
- washthe mixture was washed with saturated NaHCO3 solution (2×20 ml)
- customA precipitate precipitated out of the solution
- filtrationthis was filtered off with suction
- washThe organic phase was washed with saturated NaCl solution (2×20 ml)
- dry with materialdried over Na2SO4
- concentrationconcentrated i
Sources & evidence
- ORD record
- ord-37d91753addc4c3185b47258e9ef0c07
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138187B2
Reaction notes
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