Methanol → HCID 20274169, compound

HRID 371065Notes

Reaction equation

HRID 371065 reaction equation
B#B.[CH2:3]([N:6]([CH2:20][CH2:21][CH3:22])[C:7](=O)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:4][CH3:5].CO>O1CCCC1>[CH2:20]([N:6]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:3][CH2:4][CH3:5])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 4159886HCID 4159886, compoundHCID 6328200Diboron

Product 1

HCID 20274169HCID 20274169, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 200 ml. (0.20 mole) of a 1M solution of diborane in tetrahydrofuran cooled in an ice bath was added dropwise a solution of 27.8 g. (0.10 mole) of N,N-di-(n-propyl)-3,4-dimethoxyphenylacetamide in about 200 ml. of anhydrous tetrahydrofuran, under argon. The mixture was refluxed for one and one-quarter hours, cooled and methanol added carefully. When the bubbling subsided the reaction mixture was evaporated in vacuo. The residue was dissolved in methanol, ethereal hydrogen chloride was added and the mixture evaporated in vacuo slowly. This residue was dissolved in water, washed with ether, basified and extracted with ether. The dried solution was evaporated to yield N,N-di-(n-propyl)-3,4-dimethoxyphenethylamine.

Workup

  1. additionwas added dropwise a solution of 27.8 g
  2. temperatureThe mixture was refluxed for one and one-quarter hours
  3. temperaturecooled
  4. customwas evaporated in vacuo
  5. dissolutionThe residue was dissolved in methanol
  6. additionethereal hydrogen chloride was added
  7. customthe mixture evaporated in vacuo slowly
  8. dissolutionThis residue was dissolved in water
  9. washwashed with ether
  10. extractionextracted with ether
  11. customThe dried solution was evaporated

Sources & evidence

ORD record
ord-bed7c3f79ed246cea7c23a4df8309d01
Source dataset
uspto-grants-1985_07
Patent number
US04529604

Reaction notes

Loading…