Tryptophol → HCID 15557283, compound

Temperature

40 °C

Tryptophol (0.500 g, 3.10 mmol) and Et3N (1 mL) were dissolved in DCM (2 mL) and then mesyl chloride (0.24 mL, 3.102 mmol) was added dropwise at RT. The reaction was stirred for 3 h and then volatiles were removed in vacuo. The crude mesylate was taken up in DCM (3 mL) and to it was added 1-methylpiperazine (1.72 mL, 15.5 mmol) and Et3N (1 mL). The reaction was heated to 40° C. and stirred overnight. After completion, the reaction mixture was poured into cold water, the pH was adjusted to 10 with 1 N NaOH and the organic products were extracted with DCM (3×15 mL). The combined organic extracts were washed with brine (15 mL), dried with Na2SO4, filtered and concentrated in vacuo. Automated column chromatography method 2 was used to isolate the title compound (0.42 g, 56%). 1H NMR (400 MHz, CDCl3): δ 7.54 (d, J=7.8 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 7.10 (t, J=7.1 Hz, 1H), 7.03 (t, J=7.3 Hz, 1H), 6.98 (s, 1H), 2.87 (t, J=7.8 Hz, 2H), 2.58 (t, J=5.9 Hz, 2H), 2.38 (br, 8H), 2.17 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 136.7, 127.4, 121.8, 121.0, 118.3, 118.0, 112.4, 111.0, 58.9, 54.1, 52.2, 44.6, 22.2. ESI-HRMS: calc. for C15H21N3: [M+H]+=244.1808 m/z, found: [M+H]+=244.1797 m/z.

1. customvolatiles were removed in vacuo
2. stirringstirred overnight
3. extractionthe organic products were extracted with DCM (3×15 mL)
4. washThe combined organic extracts were washed with brine (15 mL)
5. dry with materialdried with Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-75099ce5f5734ae39b7c2ba2bfb64131

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249087B2