2-(4-Chlorophenyl)ethylamine → HCID 63717114, compound

HRID 1810095Notes

Reaction equation

HRID 1810095 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20](O)=[O:21])=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.C(OCC)(=O)C.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:20]([C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[NH:11][CH:12]=[CH:13]3)=[O:21])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 674302-(4-Chlorophenyl)ethylamineHCID 742801H-Indole-5-Carboxylic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 63717114HCID 63717114, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(4-chlorophenyl)ethylamine (0.531 g, 3.41 mmol), indole-5-carboxylic acid (0.500 g, 3.10 mmol) and DIEA (0.811 mL, 4.65 mmol) in DCM (10 mL) was added HBTU (1.29 g, 3.41 mmol) and acetonitrile (5 mL), and the reaction was stirred at ambient temperature overnight. The reaction mixture was diluted with ethyl acetate (75 mL) and the organic layer was washed with 2N HCl (50 mL) and brine (50 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0.5% methanol/DCM to 10% methanl/DCM to provide N-(4chlorophenethyl)-1H-indole-5carboxamide (0.650 g, 70.1% yield) as waxy yellow solid.

Workup

  1. washthe organic layer was washed with 2N HCl (50 mL) and brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 0.5% methanol/DCM to 10% methanl/DCM

Sources & evidence

ORD record
ord-0da162c079d14b969a6f9c7bdec840b8
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

Loading…