2-(4-Chlorophenyl)ethylamine → HCID 178432229, compound

HRID 1810107Notes

Reaction equation

HRID 1810107 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:4]=2[N:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH:23][C:11]([C:9]2[CH:8]=[CH:7][C:5]3[NH:6][C:2]([CH3:1])=[N:3][C:4]=3[CH:10]=2)=[O:13])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 11326092-methyl-1H-benzimidazole-5-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 178432229HCID 178432229, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-methyl-1H-benzo[d]imidazole-5carboxylic acid (0.750 g, 4.26 mmol), 2-(4-chlorophenyl)ethanamine (0.596 g, 3.83 mmol), HBTU (1.78 g, 4.68 mmol) and DIEA (1.11 mL, 6.39 mmol) in 10 mL of DCM was stirred at ambient temperature overnight. To the reaction was added DMF (10 mL) which caused a clear solution to form. The reaction was loaded onto a silica gel samplet and the product eluted using a gradient of 0.5% MeOH/DCM to 10% MeOH/DCM. Isolated N-(4-chlorophenethyl)-2-methyl-1H-benzo[d]imidazole-5carboxamide (0.65 g, 48.7% yield) as a yellow oil. MS(ESI)=314.4 (M+1).

Workup

  1. customto form
  2. washthe product eluted

Sources & evidence

ORD record
ord-4c403a8b90b54c4ebc8cf583a53200ec
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

Loading…