Dimethylformamide → 5,5-Dimethyl-3-morpholin-4-yl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

HRID 1687661Notes

Reaction equation

HRID 1687661 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN(C=O)C.[H-].[Na+].I[CH:15]1[CH2:21][C:20]([CH3:23])([CH3:22])[C:19]2[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:18]=2[NH:17][C:16]1=[O:31]>>[CH3:22][C:20]1([CH3:23])[C:19]2[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:18]=2[NH:17][C:16](=[O:31])[CH:15]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH2:21]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 24758Sodium hydrideHCID 672643563-Iodo-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

Product 1

HCID 672635305,5-Dimethyl-3-morpholin-4-yl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

Conditions

Temperature
0 °C

Procedure

Morpholine (0.0726 mL, 0.000833 mol) was dissolved in DMF (45 mL, 0.58 mol) and cooled to 0° C., and to this solution was added Sodium hydride, 60% disp. in mineral oil (40.0 mg). This mixture was allowed to stir for 30 minutes, followed by the addition of 3-Iodo-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one (300 mg, 0.0008 mol). The reaction was allowed to warm to rt for 16 h. The reaction was quenched by the addition of ice & water, partitioned between water and EtOAc, extracted 3× with 30 mL portions of EtOAc, was dried over MgSO4, filtered, and concentrated under reduced pressure. (87 mg, 30%). LCMS 320 (M+H)

Workup

  1. temperatureto warm to rt for 16 h
  2. customThe reaction was quenched by the addition of ice & water
  3. custompartitioned between water and EtOAc
  4. extractionextracted 3× with 30 mL portions of EtOAc
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02ca007b7d304d0c9053e1cdc3d9ea0e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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