Morpholine → HCID 23035242, compound

HRID 1709968Notes

Reaction equation

HRID 1709968 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[C:19]([O:20][CH3:21])=[CH:18][C:12]2[S:13][C:14]([CH:16]=O)=[CH:15][C:11]=2[CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C-:34]#[N:35].[K+].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH3:7][O:8][C:9]1[C:19]([O:20][CH3:21])=[CH:18][C:12]2[S:13][C:14]([CH:16]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:34]#[N:35])=[CH:15][C:11]=2[CH:10]=1

Participants

8

Reactant 5

HCID 8083MorpholineHCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23035258HCID 23035258, compound

Product 1

HCID 23035242HCID 23035242, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

Morpholine (10.8 ml) was added to a stirred suspension of 5,6-dimethoxy-benzo[b]thiophene-2-carboxaldehyde (5.0 g) and p-toluenesulphonic acid monohydrate (4.3 g) in dry dioxan (43 ml) under an atmosphere of nitrogen. The mixture was heated at reflux for 30 min. and then the resultant solution was cooled to 50° C. and treated in one portion with a suspension of potassium cyanide (1.46 g) in water (2.5 ml). The reaction mixture was heated at reflux for 1 hour then cooled to room temperature and treated with 15% w/v potassium carbonate in water (20 ml). The reaction mixture was then diluted with water (200 ml) and the resultant precipitate was filtered and dried to give 2-(5,6-dimethoxy-benzo[b]thien-2-yl)-2-(4-morpholinyl)acetonitrile as a pale yellow solid (6.54 g). A portion crystallized from dichloromethane/diethyl ether had m.p. 196°-199° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 min.
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 1 hour
  5. filtrationthe resultant precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-ef7dd2b3d9924e5c834b0bd5d97fb853
Source dataset
uspto-grants-1990_08
Patent number
US04952571

Reaction notes

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