Triethylamine → 3-[1-(1-indanylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole

HRID 1267156Notes

Reaction equation

HRID 1267156 reaction equation
[CH:1]1([C:10](Cl)=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH:13]1[CH2:18][CH:17]=[C:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.C(N(CC)CC)C.[NH4+].[OH-]>ClCCl.C1COCC1>[CH:1]1([C:10]([N:13]2[CH2:14][CH:15]=[C:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:17][CH2:18]2)=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 13953782Indane-1-carboxylic acid chloride

Product 1

HCID 185458823-[1-(1-indanylcarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indoleYield 55.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Indanecarboxylic acid chloride (4.5 g), prepared as described in International Patent Application No. WO 9533721-A1 in dichloromethane (25 ml) was added drop-wise at 0-5° C. to a mixture of 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (5 g) (see general method for preparation in Guillaume et al. Eur. J. Med. Chem. 1987, 22, 33-43) and triethylamine (3.8 ml) in THF (50 ml). The resulting mixture was stirred overnight at room temperature. The mixture was poured into diluted aqueous NH4OH (500 ml) and extracted several times with dichloromethane (4×100 ml). The combined organic phases were worked up according to the general procedure above. Column chromatography (eluted with ethyl acetate/heptane 70/30) of the crude product afforded pure title compound 4a as a visceous oil (4.7 g) which was used without further purification.

Workup

  1. extractionextracted several times with dichloromethane (4×100 ml)
  2. washColumn chromatography (eluted with ethyl acetate/heptane 70/30) of the crude product

Sources & evidence

ORD record
ord-968fcefc4deb4b80b552e2bae992a195
Source dataset
uspto-grants-2003_04
Patent number
US06552044B2

Reaction notes

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