Cyclohexylamine → HCID 67821850, compound

HRID 1034277Notes

Reaction equation

HRID 1034277 reaction equation
[N:1]1([CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([O-:17])=O)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[K+].[CH:21]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C>[CH:21]1([NH:27][C:15](=[O:17])[C:14]2[CH:13]=[CH:12][C:11]([CH2:10][N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[CH:2]3)=[CH:19][CH:18]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67821791HCID 67821791, compound

Product 1

HCID 67821850HCID 67821850, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-5 °C

Procedure

A stirred suspension of crude potassium 4-(1H-benzimidazylmethyl)benzoate (0.49 g, 1.7 mmol) in dry DMF (10 ml) under argon was treated with cyclohexylamine (0.2 g, 2.0 mmol) and triethylamine (0.34 g, 3.4 mmol). The solution was cooled to -5° C. and DPPA (0.53 g, 1.9 mmol) in DMF (10 ml) was added. The solution was allowed to warm to room temperature, stirred overnight and concentrated to give the crude product. Chromatography (silica gel, ethyl acetate) followed by crystallisation from toluene gave N-cyclohexyl 4-(1H-benzimidazylmethyl)benzamide (91 mg, 16%) as a white crystalline solid.

Workup

  1. temperatureto warm to room temperature
  2. concentrationconcentrated
  3. customto give the crude product
  4. customChromatography (silica gel, ethyl acetate) followed by crystallisation from toluene

Sources & evidence

ORD record
ord-d7e49bb98baa45dda207ffc652e21ca5
Source dataset
uspto-grants-1994_05
Patent number
US05314880

Reaction notes

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