Dimethylformamide → HCID 18963759, compound

HRID 2226830Notes

Reaction equation

HRID 2226830 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:7])[CH:5]=[O:6].[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27]C4NC(=O)[CH2:32][CH2:31][CH2:30][C:29]=4[CH:36]=3)[CH2:19][CH2:18]2)=[N:9]1.CI>CCCCC>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([N:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:3]4[N:4]([CH3:7])[C:5](=[O:6])[CH2:32][CH2:31][CH2:30][C:29]=4[CH:36]=3)[CH2:21][CH2:22]2)=[N:9]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15056387HCID 15056387, compound2×

Product 1

HCID 18963759HCID 18963759, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Under nitrogen, sodium hydride (20 mg, 0.5 mmol, 60% oil dispersed) was washed free of oil with pentane and layered with 6 ml dimethylformamide. In one portion, 155 mg (0.38 mmol) 7-(2-(4-(1,2-benzisothiazol-3-yl)piperazinyl)ethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (the title compound of Example 54) was added and stirring was continued for 0.5 hours at 25° C. To the solution was then added methyl iodide (162 mg, 1.14 mmol) and stirring was continued overnight. After pouring over 60 ml ice/water, the product was extracted with 40 ml ethyl acetate which was washed with water (2×50 ml), dried with sodium sulfate and concentrated to an oil, 54 mg. Chromatography (32-63 micron silica gel) eluting with 2% methanol in methylene dichloride provided the pure free base, 46 mg (29%).

Workup

  1. waitwas continued overnight
  2. extractionthe product was extracted with 40 ml ethyl acetate which
  3. washwas washed with water (2×50 ml)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated to an oil, 54 mg
  6. washChromatography (32-63 micron silica gel) eluting with 2% methanol in methylene dichloride
  7. customprovided the pure free base, 46 mg (29%)

Sources & evidence

ORD record
ord-6fd4c905d05f4922b170866b94d91bfa
Source dataset
uspto-grants-1994_09
Patent number
US05350747

Reaction notes

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