1,2-Dichloroethane → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-4-yl)propyl)piperidine-4-carboxamide

HRID 83634Notes

Reaction equation

HRID 83634 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C(Cl)CCl.CCN(C(C)C)C(C)C.[N:52]1[CH:57]=[CH:56][C:55]([CH:58]([CH3:61])[CH2:59][NH2:60])=[CH:54][CH:53]=1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:60][CH2:59][CH:58]([C:55]3[CH:56]=[CH:57][N:52]=[CH:53][CH:54]=3)[CH3:61])=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 433168142-(Pyridin-4-yl)propan-1-amineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 665713381-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(2-(pyridin-4-yl)propyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (0.350 g, 0.882 mmol), 1-hydroxybenzotriazole (0.149 g, 1.103 mmol), and EDC (0.211 g, 1.103 mmol) were dissolved in 3.0 mL of DCM. The reaction was allowed to stir at room temperature for 15 minutes before adding Hunig's Base (0.321 mL, 1.838 mmol) and 2-(pyridin-4-yl)propan-1-amine (0.100 g, 0.735 mmol) as a 2 mL DCM solution. The reaction was allowed to stir overnight. The reaction was dissolved in water and ethyl acetate. The organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride. It was then dried over magnesium sulfate, filtered and concentrated. The crude material was triturated in ethyl acetate to obtain product. (Yield: 151 mg) 1H-NMR (500 MHz, CDCl3) 8.59-8.51, 7.65, 7.34, 7.22-7.12, 7.06-6.99, 6.62, 5.46, 5.31, 4.69-4.03, 3.64-3.53, 3.36-3.27, 3.06-2.95, 2.89-2.78, 2.23-2.13, 1.87-1.25

Workup

  1. stirringto stir overnight
  2. washThe organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride
  3. dry with materialIt was then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was triturated in ethyl acetate
  7. customto obtain product

Sources & evidence

ORD record
ord-0d93398541bc4f88a17b2a183f688af5
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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