Phenethylamine → HCID 57385299, compound

HRID 83630Notes

Reaction equation

HRID 83630 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.[C:59]1([CH2:65][CH2:66][NH2:67])[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=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:67][CH2:66][CH2:65][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 57385299HCID 57385299, compound

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 (97 mg, 0.504 mmol), and 1-hydroxybenzotriazole (68.1 mg, 0.504 mmol) were dissolved in DCM (Volume: 3.0 ml). The reaction was stirred at room temperature for 10 minutes before Hunig's Base (0.088 ml, 0.504 mmol) and 2-phenylethanamine (0.063 ml, 0.504 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 recrystallized in ether and ethyl acetate to obtain product as a white solid. (Yield: 76 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.85, 7.62, 7.53, 7.36-7.05, 6.71, 5.48, 4.38, 4.01, 3.26, 2.90, 2.69, 2.39-2.28, 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 recrystallized in ether
  7. customethyl acetate to obtain product as a white solid

Sources & evidence

ORD record
ord-837c3626a76e47a89c7a97325dd02894
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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