Tryptamine → HCID 19590181, compound

HRID 1771072Notes

Reaction equation

HRID 1771072 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.CCN(CC)CC.[S:20](Cl)([CH3:23])(=[O:22])=[O:21]>C(Cl)Cl>[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:20]([CH3:23])(=[O:22])=[O:21])=[CH:5]1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 19590181HCID 19590181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask charged with tryptamine (2.0 g, 12.5 mmol) in DCM (20 mL) was added Et3N (3.5 mL, 25 mmol) under an atmosphere of Ar and cooled to 0° C. The solution was then added mesyl chloride (1.5 mL, 18.7 mmol) and the resulting reaction mixture was stir to RT for 2 h. The reaction was quenched with water (20 mL) and extracted with DCM (3×20 mL). The combined organic extracts were washed with brine (30 mL), dried over Na2SO4 and concentrated in vacuo. The desired product was purified via automated column chromatography method 2 (2.1 g, 70%) and isolated as a brown oil. 1H NMR (400 MHz, MeOD) δ 7.55 (d, J=7.6 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H), 7.08 (m, 2H), 7.01 (td, J=8.0, 0.8 Hz, 1H), 3.35 (t, J=7.2 Hz, 2H), 2.99 (t, J=7.2 Hz, 2H), 2.76 (s, 3H). 13C NMR (100 MHz, MeOD) δ 138.28, 128.77, 123.91, 122.54, 119.85, 119.34, 112.93, 112.43, 45.09, 40.02, 27.60.

Workup

  1. customThe reaction was quenched with water (20 mL)
  2. extractionextracted with DCM (3×20 mL)
  3. washThe combined organic extracts were washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe desired product was purified
  7. customisolated as a brown oil

Sources & evidence

ORD record
ord-8784115317484ae0ac094b2dc24daa8e
Source dataset
uspto-grants-2016_02
Patent number
US09249087B2

Reaction notes

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