2-(4-Chlorophenyl)ethylamine → HCID 178523202, compound

HRID 1810106Notes

Reaction equation

HRID 1810106 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[N:3]=[CH:2]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.[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][NH2:55])=[CH:49][CH:48]=1>CN(C=O)C.O.CO>[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][NH:55][C:10]([C:8]2[CH:7]=[CH:6][C:5]3[NH:1][CH:2]=[N:3][C:4]=3[CH:9]=2)=[O:12])=[CH:49][CH:48]=1

Participants

8

Reactant 4

HCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524171HCID 178524171, compound

Product 1

HCID 178523202HCID 178523202, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1H-benzo[d]imidazole-5carboxylic acid (1.00 g, 6.17 mmol) and HBTU (2.57 g, 6.78 mmol) in 10 mL DMF was added DIEA (1.29 mL, 7.40 mmol) followed by 2-(4-chlorophenyl)ethanamine (1.15 g, 6.78 mmol). The reaction was stirred overnight and then diluted with water. The reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, filtered and concentrated onto silica gel. The residue was purified by flash column chromatography, eluting with 12:1 DCM:MeOH, to provide N-(4chlorophenethyl)-1H-benzo[d]imidazole-5-carboxamide (0.944 g, 6.17 mmol, 51%) as a light pink solid. MS (APCI)=300.3 (M+1).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated onto silica gel
  6. customThe residue was purified by flash column chromatography
  7. washeluting with 12:1 DCM

Sources & evidence

ORD record
ord-767c6aef90da483bb3f6685097d8d398
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

Loading…