Hydrochloric Acid → HCID 11452876, compound

HRID 1437520Notes

Reaction equation

HRID 1437520 reaction equation
[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH:10]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9][CH2:8][CH2:7][C:6]2=1.[CH:25](N(C(C)C)CC)(C)C.CI.Cl>C1COCC1>[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH:10]([N:16]([CH3:25])[CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9][CH2:8][CH2:7][C:6]2=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 2838377HCID 2838377, compound

Product 1

HCID 11452876HCID 11452876, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7d4f24cb8fe442a6904fdd769dd63de9
Source dataset
uspto-grants-2009_11
Patent number
US07622494B2

Reaction notes

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