Morpholine → 5-Cyano-2-morpholino-2,3-dihydro-3,3-dimethylbenzofuran

HRID 1155981Notes

Reaction equation

HRID 1155981 reaction equation
Cl[CH:2]1[C:6]([CH3:8])([CH3:7])[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3]1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>>[C:13]([C:10]1[CH:11]=[CH:12][C:4]2[O:3][CH:2]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:6]([CH3:8])([CH3:7])[C:5]=2[CH:9]=1)#[N:14]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 205362092-Chloro-5-cyano-2,3-dihydro-3,3-dimethylbenzofuran

Product 1

HCID 205362115-Cyano-2-morpholino-2,3-dihydro-3,3-dimethylbenzofuran

Procedure

2-Chloro-5-cyano-2,3-dihydro-3,3-dimethylbenzofuran (4.1 g), prepared as in Example 45 was heated under reflux at about 130° C. in morpholine (20 ml) for 4 hours. Addition to ice-water, followed by extraction with diethyl ether, gave, after water washing, drying over sodium sulphate and running down, 3.3 g of crude title product. Recrystallisation from isopropanol gave 2.3 g of pure product, mp 105°-107° C.

Workup

  1. temperaturewas heated
  2. extractionfollowed by extraction with diethyl ether
  3. customgave
  4. dry with materialafter water washing, drying over sodium sulphate
  5. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-47f676f71b72439ba86cb229d3c3adf9
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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