Tetrahydrofuran → HCID 13662753, compound

HRID 371067Notes

Reaction equation

HRID 371067 reaction equation
B#B.O1CCCC1.[Cl:8][C:9]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[CH:18][C:10]=1[CH2:11][CH2:12][NH:13][C:14](=O)[CH2:15][CH3:16]>CO>[CH2:14]([NH:13][CH2:12][CH2:11][C:10]1[CH:18]=[CH:19][C:20]([O:24][CH3:25])=[C:21]([O:22][CH3:23])[C:9]=1[Cl:8])[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 6328200DiboronHCID 13662750HCID 13662750, compound

Product 1

HCID 13662753HCID 13662753, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 100 ml. of a solution of diborane in tetrahydrofuran (0.93 molar, 0.093 mole) was added a solution of 9.0 g. (0.033 mole) of the above-prepared propionamide. The mixture was refluxed overnight, cooled and methanol added to destroy unreacted diborane. Ethereal hydrogen chloride and methanol were added and the mixture evaporated to dryness. The residue was dissolved in dilute hydrochloric acid/ether and the acidic aqueous solution was basified, extracted with ether and the dried ether extract evaporated to yield N-(n-propyl)-2-chloro-3,4-dimethoxyphenethylamine. The latter (3.5 g., 0.0137 mole) was dissolved in 100 ml. of propionic anhydride and stirred overnight. The mixture was evaporated nearly to dryness, toluene was added and then further evaporated to leave N-(2-chloro-3,4-dimethoxyphenethyl)-N-(n-propyl)propionamide.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperaturecooled
  3. customto destroy unreacted diborane
  4. additionEthereal hydrogen chloride and methanol were added
  5. customthe mixture evaporated to dryness
  6. dissolutionThe residue was dissolved in dilute hydrochloric acid/ether
  7. extractionextracted with ether
  8. extractionthe dried ether extract
  9. customevaporated

Sources & evidence

ORD record
ord-9797951c69bd4be1bd1ef72c8c2a53bc
Source dataset
uspto-grants-1985_07
Patent number
US04529604

Reaction notes

Loading…