Cyclohexylamine → 4-(Chloromethyl)-N-cyclohexylbenzamide

HRID 911454Notes

Reaction equation

HRID 911454 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:19]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl.Cl>[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:25][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 431562134-(Chloromethyl)-N-cyclohexylbenzamideYield 95.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To 4-chloromethylbenzoyl chloride (1.03 g, 5.47 mmol) in DCM (20 mL) at 0° C., add with stirring triethylamine (0.839 mL, 6.02 mmol) followed by cyclohexylamine (0.688 mL, 6.02 mmol), and continue stirring for 15 min. Dilute the reaction mixture with aqueous 1M hydrochloric acid, extract three times with EtOAc, wash with water and saturated aqueous NaHCO3. Dry the combined organic extracts over anhydrous Na2SO4 and concentrate in vacuo to give the title compound as a white solid (1.31 g, 95%).

Workup

  1. extractionextract three times with EtOAc
  2. washwash with water and saturated aqueous NaHCO3
  3. dry with materialDry the combined organic extracts over anhydrous Na2SO4
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-4ed79dd295a64e48902ac183786dfb7b
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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