Formic Acid → HCID 19970870, compound

HRID 975169Notes

Reaction equation

HRID 975169 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:33]=[CH:32][C:22]3[NH:23][C:24]4[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=4[CH2:26][CH2:27][C:21]=3[CH:20]=2)[CH2:14][CH2:13]1.CO>ClC(Cl)C>[CH:1]([N:23]1[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[CH2:26][CH2:27][C:21]2[CH:20]=[C:19]([CH2:18][N:15]3[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]3)[CH:33]=[CH:32][C:22]1=2)=[O:3]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 887MethanolHCID 7918Acetic AnhydrideHCID 30488975H-Dibenz(b,f)azepine, 10,11-dihydro-2-((4-methyl-1-piperazinyl)methyl)-

Product 1

HCID 19970870HCID 19970870, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
45 °C

Procedure

Formic acid (99%; 300 ml) was added dropwise to 600 ml of acetic anhydride, the internal temperature being maintained at 45° C. followed by stirring for one hour To this solution was added, in small portions, a suspension of 375 g of Compound 30-1a in 500 ml of dichloroethane under ice cooling, followed by stirring at room temperature for 8 hours. After cooling, 400 ml of methanol was added, and the solvent was distilled off under reduced pressure. The residue was diluted with water, and adjusted to pH 9-10 with a 10N aqueous solution of sodium hydroxide. The organic layer was extracted with ethyl acetate, and the extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent:ethyl acetate/methanol/triethylamine (300/20/1)] to give 106.8 g (23%) of the product as an oily substance.

Workup

  1. additionwas added, in small portions
  2. stirringby stirring at room temperature for 8 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe residue was diluted with water
  6. extractionThe organic layer was extracted with ethyl acetate
  7. washthe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography [eluent:ethyl acetate/methanol/triethylamine (300/20/1)]

Sources & evidence

ORD record
ord-8ab38990c2794c6d9cda4c2e98cd79e3
Source dataset
uspto-grants-1997_03
Patent number
US05607955

Reaction notes

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