Sodium Hydroxide → 2-ethyl-5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1751796Notes

Reaction equation

HRID 1751796 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([F:12])=[CH:7][CH:6]=2)[CH3:2].[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[OH-].[Na+]>C(O)(=O)C.P(=O)(O)(O)O>[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[C:16]1[CH2:17][CH2:18][NH:13][CH2:14][CH:15]=1)=[CH:9][C:8]([F:12])=[CH:7][CH:6]=2)[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 337214-PiperidoneHCID 205171722-ethyl-5-fluoro-1H-indole

Product 1

HCID 666697172-ethyl-5-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 67.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1004Phosphoric AcidSolvent

Conditions

Temperature
90 °C

Procedure

2.83 g 2-ethyl-5-fluoro-1H-indole are suspended in 50 ml acetic acid and heated to 90° C. A suspension of 6.66 g 4-piperidone in 15 ml phosphoric acid 2N is added. The reaction mixture is stirred for 3 hours at 90° C., combined with sodium hydroxide solution and the product is extracted with ethyl acetate. 2.85 g product are obtained in the form of a solid. 1H NMR (400 MHz, DMSO): 5.63 (1H, s); 2.73 (2H, q); 1.23 (3H, t).

Workup

  1. additionis added
  2. extractionthe product is extracted with ethyl acetate

Sources & evidence

ORD record
ord-70129054d1df47a4a35e4b15cd2a0e5f
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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