Triethylamine → 5-methoxy-3-[N-(3-(4-fluoro-phenyl)-3-oxo-propyl)-1,2,5,6-tetrahydro-pyridin-3-ylmethyl]-1H-indole

HRID 355993

Reaction equation

HRID 355993 reaction equation
C(N(CC)CC)C.Cl[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[O:12].[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[C:25]2[CH2:31][C:32]1[CH2:33][NH:34][CH2:35][CH2:36][CH:37]=1>C(OCC)C.C(Cl)Cl>[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[C:25]2[CH2:31][C:32]1[CH2:33][N:34]([CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:12])[CH2:35][CH2:36][CH:37]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 676722-Chloro-4'-fluoropropiophenoneHCID 189408175-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole

Product 1

HCID 189408815-methoxy-3-[N-(3-(4-fluoro-phenyl)-3-oxo-propyl)-1,2,5,6-tetrahydro-pyridin-3-ylmethyl]-1H-indole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.9 ml; 0.0063 mol) was added to a solution of 3-chloro-4'-fluoropropiophenone (1.2 g; 0.0063 mol) in diethyl ether (10 ml). The resulting mixture was stirred for 3 hours at room temperature. Then the mixture was filtered and the filtrate was concentrated under vacuum. The residue was taken up with a mixture of compound of Description 5 [5-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole] (0.79 g; 0.0028 mol), triethylamine (0.8 ml; 0.0057 mol) in methylene chloride (20 ml). The reaction mixture was refluxed for 4 hours. Then the reaction was concentrated under vacuum and the residue was triturated with 1N hydrochloric acid. The aqueous phase was decanted, and the guming solid was twice washed with water and triturated with diethyl ether. The title compound hydrochloride was collected by filtration, washed with diethyl ether and recrystallized with a mixture (1/2) of ethyl acetate/acetone. 0.86 g of the desired compound were obtained.

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. temperatureThe reaction mixture was refluxed for 4 hours
  4. concentrationThen the reaction was concentrated under vacuum
  5. customthe residue was triturated with 1N hydrochloric acid
  6. customThe aqueous phase was decanted
  7. washthe guming solid was twice washed with water
  8. customtriturated with diethyl ether
  9. filtrationThe title compound hydrochloride was collected by filtration
  10. washwashed with diethyl ether
  11. customrecrystallized with a mixture (1/2) of ethyl acetate/acetone

Sources & evidence

ORD record
ord-5ea039a5f66049a6a1bef76935a1c5c5
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Linked notes

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