Acetonitrile → N-(p-Chloro-N-cyclohexylbenzimidoyl)-morpholine hydrochloride

HRID 917942Notes

Reaction equation

HRID 917942 reaction equation
C(Cl)([Cl:3])=O.[CH:5]1([NH:11][C:12](=O)[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(#N)C>O1CCCC1>[ClH:3].[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[N:11][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6371PhosgeneHCID 8083MorpholineHCID 2254614-Chloro-N-cyclohexylbenzamide

Product 1

HCID 21524393N-(p-Chloro-N-cyclohexylbenzimidoyl)-morpholine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold solution of 9.6 gm. (0.096 mole) of phosgene in tetrahydrofuran is added in one portion 19.0 gm. (0.08 mole) of N-cyclohexyl-p-chlorobenzamide. After ten minutes the reaction mixture is allowed to warm to room temperature, stirred overnight, and the mixture concentrated to a solid in vacuo with a bath temperature of 30°. The crude residue is suspended in 250 ml. of acetonitrile, cooled to 0° and treated with a solution of 28.0 gm. (0.32 mole) of morpholine in 100 ml. of acetonitrile. After allowing the reaction mixture to warm to room temperature it is heated at reflux for two hours, concentrated in vacuo to an oil and suspended in ether. A precipitate is collected and shown to be starting material. The filtrate is concentrated in vacuo, the residue taken up in acetone and treated with excess dry HCl in ether. Ether is added to the cloud point and the mixture cooled to give 3.7 gm. (13.5%) m.p. 278°-279°.

Workup

  1. waitAfter ten minutes the reaction mixture is allowed
  2. concentrationthe mixture concentrated to a solid in vacuo with a bath temperature of 30°
  3. temperatureof acetonitrile, cooled to 0°
  4. additiontreated with a solution of 28.0 gm
  5. temperatureto warm to room temperature it
  6. temperatureis heated
  7. temperatureat reflux for two hours
  8. concentrationconcentrated in vacuo to an oil
  9. customA precipitate is collected
  10. concentrationThe filtrate is concentrated in vacuo
  11. additiontreated with excess dry HCl in ether
  12. additionEther is added to the cloud point
  13. temperaturethe mixture cooled
  14. customto give 3.7 gm

Sources & evidence

ORD record
ord-4448fb654edc4f7788eb259d0fd3a833
Source dataset
uspto-grants-1976_07
Patent number
US03968211

Reaction notes

Loading…