Dimethylformamide → HCID 14155426, compound

HRID 648926Notes

Reaction equation

HRID 648926 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[CH3:11][N:12]1[CH2:33][CH2:32][N:15]2[C:16]3[CH:31]=[CH:30][CH:29]=[CH:28][C:17]=3[CH2:18][N:19]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH:21]=[C:20]3[CH:14]2[CH2:13]1>C(Cl)Cl>[CH3:11][N:12]1[CH2:33][CH2:32][N:15]2[C:16]3[CH:31]=[CH:30][CH:29]=[CH:28][C:17]=3[CH2:18][N:19]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:21]([CH:3]=[O:4])=[C:20]3[CH:14]2[CH2:13]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 14155424HCID 14155424, compound

Product 1

HCID 14155426HCID 14155426, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the reagent made from 0.56 ml of dimethylformamide in 5 ml methylene chloride and 1.03 g of phosphorous oxychloride is added a solution of 1.88 g of 1,3,4,16b-tetrahydro-2-methyl-2H,10H-indolo[2,1-c]pyrazino[1,2-a][1,4]-benzodiazepine in 5 ml methylene chloride in a dropwise manner maintaining the temperature of the reaction below 10°. The reaction is allowed to stir at room temperature for 30 minutes. The reaction mixture is quenched with 10 ml of a saturated solution of sodium acetate and heated at reflux temperature for 1 hour. On cooling to room temperature the reaction is extracted with 3×50 ml methylene chloride. The organic extracts are combined and dried over anhydrous sodium sulfate and the solvent removed by evaporation under reduced pressure to yield 1,3,4,16b-tetrahydro-2-methyl-2H,10H-indolo[2,1-c]pyrazino[1,2-a][1,4]benzodiazepine-16-carboxaldehyde which is converted to the hydrochloride salt, mp 260°-266°.

Workup

  1. temperaturemaintaining
  2. customthe temperature of the reaction below 10°
  3. customThe reaction mixture is quenched with 10 ml of a saturated solution of sodium acetate
  4. temperatureheated
  5. temperatureat reflux temperature for 1 hour
  6. temperatureOn cooling to room temperature the reaction
  7. extractionis extracted with 3×50 ml methylene chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-a41948af24c54d0894caf724ea1aa62c
Source dataset
uspto-grants-1988_04
Patent number
US04737496

Reaction notes

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