Hydrochloric Acid → HCID 11293048, compound

HRID 1437521Notes

Reaction equation

HRID 1437521 reaction equation
[CH3:1]I.[ClH:3].[Br:4][C:5]1[CH:6]=[C:7]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]1[CH:12]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:11][CH2:10][CH2:9][C:8]2=1.[H-].[Na+].Cl>C1COCC1>[ClH:3].[Br:4][C:5]1[CH:6]=[C:7]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:1])[C:13]1[CH:12]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:11][CH2:10][CH2:9][C:8]2=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2838377HCID 2838377, compound

Product 1

HCID 11293048HCID 11293048, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6-Bromo-9-methyl-N-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride salt was prepared by addition of methyl iodide (0.016 mL, 0.25 mmol) to a solution of 6-bromo-N-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride salt (0.05 g, 0.12 mmol) and sodium hydride (0.04 mL, 0.25 mmol) in THF (2.0 mL) that was under inert atmosphere and cooled to 0° C. The mixture was allowed to warm to room temperature and stirred for 12 hrs. The reaction was quenched with saturated (“sat.”) ammonium chloride (“NH4Cl”) (2.0 mL), ethyl acetate was added (10 mL), the organic layer was separated and washed with sat. NaCl (2.0 mL), dried over sodium sulfate (“Na2SO4”), filtered and evaporated to leave an oily residue. Purification by flash chromatography with 10-50% gradient ethyl acetate/hexanes eluent afforded a clear oil that was converted to the HCl salt to give a white solid (0.005 g, 9%). 1H-NMR (CDCl3): δ 7.57 (s, 1H), 7.31-7.21 (m, 7H), 7.09 (d, 1H), 3.86 (m, 1H), 3.53 (s, 3H), 3.19-3.13 (m, 1H), 2.94-2.87 (m, 1H), 2.84-2.80 (m, 2H), 2.74-2.67 (m, 1H), 2.55-2.47 (m, 1H), 2.17-2.11 (m, 1H), 1.83-1.70 (m, 3H); MS m/z 381, 383 (M−1).

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with saturated (“sat.”) ammonium chloride (“NH4Cl”) (2.0 mL), ethyl acetate
  3. additionwas added (10 mL)
  4. customthe organic layer was separated
  5. washwashed with sat. NaCl (2.0 mL)
  6. dry with materialdried over sodium sulfate (“Na2SO4”)
  7. filtrationfiltered
  8. customevaporated
  9. customto leave an oily residue
  10. customPurification by flash chromatography with 10-50% gradient ethyl acetate/hexanes eluent
  11. customafforded a clear oil that

Sources & evidence

ORD record
ord-aa19b7635f9b484fad04584a12c60955
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

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