Morpholine → HCID 19815935, compound

HRID 2247875Notes

Reaction equation

HRID 2247875 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[C:8]([CH3:27])=[N:9][C:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=1)=[O:5].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C(Cl)Cl.O1CCCC1>[C:19]([C:15]1[CH:14]=[C:13]([C:12]2[CH:11]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=[C:8]([CH3:27])[C:7]=2[NH:6][C:4](=[O:5])[CH2:3][CH2:2][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:18]=[CH:17][CH:16]=1)#[N:20]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 19815939HCID 19815939, compound

Product 1

HCID 19815935HCID 19815935, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(3-chloropropionylamino)-4-(3-cyanophenyl)-2-methyl-6-phenylpyridine (0.45 g) and morpholine (0.23 g) in a mixture of methylene chloride (5 ml) and tetrahydrofuran (10 ml) was refluxed for 8 hours. The mixture was concentrated, diluted with water (20 ml) and chloroform (20 ml). The separated organic layer was washed with water, dried and concentrated in vacuo. The residue was triturated with diethyl ether to give 4-(3-cyanophenyl)-2-methyl-3-(3-morpholinopropionylamino)-6-phenylpyridine (0.45 g).

Workup

  1. temperaturewas refluxed for 8 hours
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water (20 ml) and chloroform (20 ml)
  4. washThe separated organic layer was washed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-1d7dfbf37a984ca081ade1b5b1680691
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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