Hydrochloric Acid → Benzamide

HRID 1462459Notes

Reaction equation

HRID 1462459 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8](C)[C@@H]2CCCC(=O)[C@H]2N2CCCC2)=[O:7])=[CH:4][CH:3]=1.COC(OC)OC.Cl>CO>[C:6]([NH2:8])(=[O:7])[C:5]1[CH:22]=[CH:23][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 22822035HCID 22822035, compound

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.0 g of trans-(±)-4-bromo-N-methyl-N-[3-oxo-2-(1-pyrrolidinyl)cyclohexyl]benzamide, prepared as described in Example 1C above, in fifty ml of dry methanol there is added 5 ml of trimethylorthoformate and 0.5 ml of 4M methanolic hydrogen chloride. The resulting mixture is refluxed for about 16 hours, cooled, and the solvent is removed in vacuo. The residual oil is crystallized from a hot methanol solution thereof diluted with diethyl ether until the mixture becomes cloudy to obtain the titled 4-bromo-N-methyl-N-[3,3-dimethoxy)-2-(1-pyrrolidinyl)cyclohexyl]benzamide, which is converted to a hydrochloride salt.

Workup

  1. temperatureThe resulting mixture is refluxed for about 16 hours
  2. temperaturecooled
  3. customthe solvent is removed in vacuo
  4. customThe residual oil is crystallized from a hot methanol solution
  5. additionthereof diluted with diethyl ether until the mixture

Sources & evidence

ORD record
ord-be0d33c8f7664739b0e578c9c58049fb
Source dataset
uspto-grants-1984_07
Patent number
US04460600

Reaction notes

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