Hydrochloric Acid → HCID 22827145, compound

HRID 1462461Notes

Reaction equation

HRID 1462461 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]([CH3:25])[C@@H:13]2C(=O)[CH2:17][CH2:16][CH2:15][C@H:14]2[N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].CO[CH:28]([O:31][CH3:32])[O:29][CH3:30].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]([CH3:25])[C@@H:13]2[C:28]([O:29][CH3:30])([O:31][CH3:32])[CH2:17][CH2:16][CH2:15][C@H:14]2[N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 22827146HCID 22827146, compound

Product 1

HCID 22827145HCID 22827145, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans-(±)-3,4-dichloro-N-methyl-N-[6-oxo-2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide, prepared as described in Part B hereinabove, in 50 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 trans-(±)-3,4-dichloro-N-methyl-N-[6,6-dimethoxy-2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide, 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. additiondiluted with diethyl ether until the mixture

Sources & evidence

ORD record
ord-5c45ba78292844cb890242f0b6f6fdc1
Source dataset
uspto-grants-1984_07
Patent number
US04460600

Reaction notes

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