Hydrochloric Acid → HCID 11452876, compound

6-Bromo-N-methyl-N-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride salt was prepared from 6-bromo-N-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride salt (0.05 g, 0.12 mmol), diisopropylethyl amine (0.04 mL, 0.25 mmol) and methyl iodide (0.008 mL, 0.12 mmol) in THF (2.0 mL). The reagents were added to a round bottom flask and allowed to stir for 12 hrs. at room temperature under inert atmosphere. The solvent was evaporated, ethyl acetate was added (10 mL), the organics were washed with water (2.0 mL) and sat. NaCl (2.0 mL), dried over Na2SO4, filtered and evaporated to leave an oily residue. Purification by flash chromatography with gradient 10-50% ethyl acetate/hexanes eluent afforded a clear oil that was converted to the HCl salt to give a white solid (0.01 g, 20%). 1H-NMR (CDCl3): δ 8.30 (s, 1H), 7.53 (d, 2H), 7.38-7.10 (m, 5H), 6.89 (d, 1H), 4.09 (m, 1H), 3.04-2.95 (m, 1H), 2.90-2.80 (m, 2H), 2.70-2.55 (m, 3H), 2.48 (s, 3H), 2.11-1.99 (m, 2H), 1.70-1.60 (m, 2H).

1. additionThe reagents were added to a round bottom flask
2. customat room temperature
3. customThe solvent was evaporated
4. additionethyl acetate was added (10 mL)
5. washthe organics were washed with water (2.0 mL) and sat. NaCl (2.0 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated
9. customto leave an oily residue
10. customPurification by flash chromatography with gradient 10-50% ethyl acetate/hexanes eluent
11. customafforded a clear oil that

ORD record

ord-7d4f24cb8fe442a6904fdd769dd63de9

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622494B2