p-Fluorophenethylamine → 1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(4-fluorophenethyl)piperidine-4-carboxamide

HRID 83623

Reaction equation

HRID 83623 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.CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[F:59][C:60]1[CH:65]=[CH:64][C:63]([CH2:66][CH2:67][NH2:68])=[CH:62][CH:61]=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:68][CH2:67][CH2:66][C:63]3[CH:64]=[CH:65][C:60]([F:59])=[CH:61][CH:62]=3)=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 4653p-FluorophenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 665712781-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(4-fluorophenethyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), EDCI (72.5 mg, 0.378 mmol), and 1-hydroxybenzotriazole (51.1 mg, 0.378 mmol) were dissolved in DCM (Volume: 3.0 ml). The reaction was stirred at room temperature for 10 minutes before Hunig's Base (0.066 ml, 0.378 mmol) and 2-(4-fluorophenyl)ethanamine (0.050 ml, 0.378 mmol) were added. The reaction was allowed to stir overnight at room temperature. The reaction was diluted with water and ethyl acetate. The organic phase was washed with 1N HCl, saturated sodium bicarbonate, and brine. The organic phase was dried over magnesium sulfate, filtered, and concentrated. The crude material was triturated with ethyl acetate to obtain product as a white solid. (Yield: 111 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.84, 7.62, 7.54, 7.36-7.30, 7.26-7.17, 7.14-7.04, 6.71, 5.49, 4.58-3.71, 3.25, 2.91, 2.69, 2.37-2.29, 1.61, 1.36

Workup

  1. additionwere added
  2. washThe organic phase was washed with 1N HCl, saturated sodium bicarbonate, and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was triturated with ethyl acetate
  7. customto obtain product as a white solid

Sources & evidence

ORD record
ord-fe4a4c7eeb004e4b963dd96e9a93c4a0
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Linked notes

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