N-Methylbenzylamine → N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

HRID 83639Notes

Reaction equation

HRID 83639 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]1)=[O:11].Cl.C(N=C=NCCCN(C)C)C.O.N1(O)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[CH3:53][NH:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:55]([N:54]([CH3:53])[C:18]([CH:15]1[CH2:14][CH2:13][N:12]([C:10]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:11])[CH2:17][CH2:16]1)=[O:20])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

9

Reactant 5

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 28398271HCID 28398271, compound

Product 1

HCID 66571403N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1H-indole-2-carbonyl)piperidine-4-carboxylic acid (1.00 g, 3.67 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.408 g, 7.34 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol hydrate (1.125 g, 7.34 mmol) were dissolved in DCM (Volume: 10 ml). The reaction was allowed to stir for 10 minutes before adding DIEA (1.283 ml, 7.34 mmol) and N-methyl-1-phenylmethanamine (0.836 ml, 7.34 mmol). 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 saturated sodium bicarbonate, 1N HCl, and saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography using 30% to 60% ethyl acetate:hexanes to obtain product. (Yield: 1.03 g, white solid) 11.53, 7.59-7.54, 7.41-7.11, 7.01, 6.76-6.70, 4.66, 4.52-4.35, 3.22-2.93, 2.76, 1.84-1.51

Workup

  1. stirringto stir overnight at room temperature
  2. washThe organic phase was washed with saturated sodium bicarbonate, 1N HCl, and saturated sodium chloride solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography
  7. customhexanes to obtain product

Sources & evidence

ORD record
ord-6a4fc7c033d541848b649e7467012ac2
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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