2-(4-Chlorophenyl)ethylamine → HCID 66571402, Verbindung

HRID 83633

Reaktionsgleichung

Reaktionsgleichung von HRID 83633
[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](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.N1(O)C2C=CC=CC=2N=N1.[Cl:51][C:52]1[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][NH2:60])=[CH:54][CH:53]=1.C(N(C(C)C)C(C)C)C>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][CH2:58][C:55]3[CH:56]=[CH:57][C:52]([Cl:51])=[CH:53][CH:54]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Komponenten

9

Edukt 5

HCID 674302-(4-Chlorophenyl)ethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 66571402HCID 66571402, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (72.5 mg, 0.378 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (51.1 mg, 0.378 mmol) were dissolved in DCM (Volume: 3.0 mL). The reaction was stirred for 10 minutes before 2-(4-chlorophenyl)ethanamine (0.053 mL, 0.378 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.066 mL, 0.378 mmol). The reaction was stirred overnight at room temperature. The reaction was diluted with water and ethyl acetate. The organic layer was washed with 1N HCl, saturated sodium bicarbonate solution, and finally saturated sodium chloride. the organic layer was then dried over magnesium sulfate, filtered and concentrated. The crude material was triturated in ethyl acetate to give the product as a white solid. (Yield: 60 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.85, 7.63, 7.54, 7.38-7.31, 7.24-7.18, 7.14-7.06, 6.71, 5.49, 4.37, 4.00, 3.26, 2.92, 2.69, 2.37-2.27, 1.76-1.22

Aufarbeitung

  1. washThe organic layer was washed with 1N HCl, saturated sodium bicarbonate solution, and finally saturated sodium chloride
  2. dry with materialthe organic layer was then dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was triturated in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-36bf2828d2b24b7dbdd48dec96b99eb0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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