Triethylamine → 1-(3-chloro-1-phenyl-propyl)-1H-indole

HRID 250193Notes

Reaction equation

HRID 250193 reaction equation
[N:1]1([CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:12]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(CC)CC)C.CS([Cl:31])(=O)=O.C([O-])(O)=O.[Na+].[Li+].[Cl-]>C(Cl)Cl>[Cl:31][CH2:12][CH2:11][CH:10]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 235559373-Indol-1-yl-3-phenyl-propan-1-ol

Product 1

HCID 580884211-(3-chloro-1-phenyl-propyl)-1H-indoleYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-indol-1-yl-3-phenyl-propan-1-ol (0.166 g, 0.66 mmol) in CH2Cl2 (20 mL) and triethylamine (0.087 g, 0.85 mmol) at 0° C. was added methanesulfonyl chloride (0.083 g, 0.72 mmol), and the mixture was stirred for 1 hour at room temperature. The reaction mixture was poured into an aqueous saturated solution of NaHCO3 (50 mL) and extracted with CH2Cl2 (2×50 mL). The organic layer was dried over Na2SO4, and the solvent was removed under vacuum. The residue was diluted in MeCN (50 mL) and treated with LiCl (0.084 g, 1.98 mmol), and the reaction mixture was heated to reflux temperature for 24 hours. The solvent was removed under vacuum and the crude product was chromatographed (SiO2, Hexanes/EtOAc, 9:1) to afford 0.145 g (81% yield) of 1-(3-chloro-1-phenyl-propyl)-1H-indole as an oil.

Workup

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was removed under vacuum
  4. additionThe residue was diluted in MeCN (50 mL)
  5. temperaturethe reaction mixture was heated
  6. temperatureto reflux temperature for 24 hours
  7. customThe solvent was removed under vacuum
  8. customthe crude product was chromatographed (SiO2, Hexanes/EtOAc, 9:1)

Sources & evidence

ORD record
ord-dbf3b3b5c36146ff8f476f6e7eaca870
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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