Triethylamine → 5-Chloro-3-[1[3-(dimethylamino)benzoyl]-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole

HRID 1016292

Reaction equation

HRID 1016292 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.[CH3:17][N:18]([CH3:28])[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[C:19]([N:18]([CH3:17])[CH3:28])[CH:20]=2)[CH2:15][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 70103423-Dimethylaminobenzoyl chloride

Product 1

HCID 184068395-Chloro-3-[1[3-(dimethylamino)benzoyl]-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indoleYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-chloro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.53 g, 2.3 mmol) (Eur. J. Med. Chem., 1987, 22, 33-43) and 3-(dimethylamino)benzoyl chloride (0.5 g, 2.3 mmol) (Chem. Pharm. Bull., 1980, 28, 2045-2051) in tetrahydrofuran was stirred and treated with triethylamine (0.64 mL, 2 eq). The mixture was stirred for 2 h, treated with aqueous sodium bicarbonate (50 mL) and extracted with ethyl acetate. The organic phase was washed with brine and dried (Na2SO4) to give the title compound (0.83 g).

Workup

  1. stirringThe mixture was stirred for 2 h
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-343eeec250434045b0a93fe0ea4fc762
Source dataset
uspto-grants-2002_11
Patent number
US06476028B1

Linked notes

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