2-Chloroaniline → 3-Phenyl-3-cyclohexanepropanamide

HRID 1107440Notes

Reaction equation

HRID 1107440 reaction equation
[C:1]1([C:7]2([CH2:13][CH2:14][C:15]([OH:17])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.ClC1C=CC=CC=1[NH2:27]>C1(C)C=CC=CC=1.C(Cl)Cl>[C:1]1([C:7]2([CH2:13][CH2:14][C:15]([NH2:27])=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 72402-ChloroanilineHCID 65578Oxalyl chlorideHCID 3439853-(1-Phenylcyclohexyl)propanoic acid

Product 1

HCID 187872433-Phenyl-3-cyclohexanepropanamideYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-phenyl-3-cyclohexanepropanoic acid (0.5 g, 2.15 mmol) and oxalyl chloride (0.3 ml, 3.01 mmol) in 5 ml of toluene was stirred for 3 hours at 35-40° C. and then at room temperature overnight. The mixture was then concentrated in vacuo to provide a yellow oil which was dissolved in 5 ml of CH2Cl2, cooled to 0° C. and treated with 2-chloroaniline. The resultant mixture was stirred at 0° C. for 2 hours and filtered. The filtrate was then washed sequentially with 1.0N HCl, NaHCO3 and brine, dried over Na2SO4, filtered and then concentrated in vacuo to provide a white solid (0.66 g, 92%). A portion of this solid was recrystallized (hexanes/CH2Cl2) to provide a white solid.

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationThe mixture was then concentrated in vacuo
  4. customto provide a yellow oil which
  5. filtrationfiltered
  6. washThe filtrate was then washed sequentially with 1.0N HCl, NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9d6d47d28324780a6ab6627012a9877
Source dataset
uspto-grants-2000_05
Patent number
US06060484

Reaction notes

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