4-Methylmorpholine → HCID 22449999, compound

HRID 2186889Notes

Reaction equation

HRID 2186889 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].S(Cl)(Cl)=O.[C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][C:36]([NH:38][CH2:39][CH:40]([CH3:42])[CH3:41])=[CH:37][C:30]=3[N:29]=2)=[CH:22][CH:21]=1)#[N:19].CN1CCOCC1>C(Cl)(Cl)Cl.ClCCl.O>[C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][C:36]([N:38]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:11](=[O:13])[CH2:10][CH2:9][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=4)=[CH:37][C:30]=3[N:29]=2)=[CH:22][CH:21]=1)#[N:19]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 24386Thionyl ChlorideHCID 93617423-(4-Cyanophenyl)-propionic acidHCID 22449994HCID 22449994, compound

Product 1

HCID 22449999HCID 22449999, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

3-(p-cyanophenyl)-propionic acid (0.69 g, 3.9 mmol) in 15 mL chloroform is combined with 1.3 mL of thionyl chloride and refluxed for 3 h. The solvent and the excess thionyl chloride are distilled off, the residue is dissolved in 10 mL of dichloromethane and added dropwise to a solution of 2-[2-(4-cyanophenyl)-ethyl]-1-methyl-5-isobutylamino-benzimidazole (1.25 g, 3.8 mmol) and 1.3 mL N-methylmorpholine in 50 mL dichloromethane. This is refluxed for 0.5 h, cooled, mixed with water and extracted into the organic phase. It is washed with dilute, aqueous NaOH and with water, dried and evaporated down. The product is further reacted without being purified.

Workup

  1. temperaturerefluxed for 3 h
  2. distillationThe solvent and the excess thionyl chloride are distilled off
  3. dissolutionthe residue is dissolved in 10 mL of dichloromethane
  4. temperatureThis is refluxed for 0.5 h
  5. temperaturecooled
  6. extractionextracted into the organic phase
  7. washIt is washed
  8. additionwith dilute
  9. dry with materialaqueous NaOH and with water, dried
  10. customevaporated down
  11. customThe product is further reacted
  12. customwithout being purified

Sources & evidence

ORD record
ord-e9d05a7dcdcc4dce8c49819abaf425a2
Source dataset
uspto-grants-2002_06
Patent number
US06407130B1

Reaction notes

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