Acetic Acid → HCID 14181059, compound

HRID 487939Notes

Reaction equation

HRID 487939 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C:10](=O)[CH2:9][CH2:8]2.[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1)[CH2:9][CH2:8]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 41360218-Methoxy-2-tetraloneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 14181059HCID 14181059, compoundYield 161.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.76 g (10 mmol) of 8-methoxy-2-tetralone, 3.00 g (30 mmol) of N-methylpiperazine and 1.80 g (30 mmol) of glacial acetic acid were refluxed in 30 ml of methanol for 4 hours. 1.30 g (20 mmol) of sodium cyanoborohydride were then added, and the mixture was refluxed for a further hour. The reaction was substantially concentrated in a rotary evaporator, taken up in tert.-butyl methyl ether, and stirred vigorously for 30 minutes in 20% strength sodium hydroxide solution. The aqueous phase was extracted carefully with tert.-butyl methyl ether. Washing the combined organic phases with water and saturated sodium chloride solution, drying over potassium carbonate, and concentrating in a rotary evaporator yielded the crude product as an oil (2.9 g). This crude product was combined with that obtained from a batch of equal size (this reaction was carried out in the presence of 3A molecular sieve, otherwise the same) and chromatographed on silica gel (toluene/methanol 4:1). 4.20 g of the title compound were obtained in this fashion as a brownish oil (80%).

Workup

  1. temperaturethe mixture was refluxed for a further hour
  2. concentrationThe reaction was substantially concentrated in a rotary evaporator
  3. extractionThe aqueous phase was extracted carefully with tert.-butyl methyl ether
  4. washWashing the combined organic phases with water and saturated sodium chloride solution
  5. dry with materialdrying over potassium carbonate
  6. concentrationconcentrating in a rotary evaporator
  7. customyielded the crude product as an oil (2.9 g)
  8. customthat obtained from a batch of equal size (this reaction
  9. customotherwise the same) and chromatographed on silica gel (toluene/methanol 4:1)

Sources & evidence

ORD record
ord-a3d99723eebb4ff783986e8177741565
Source dataset
uspto-grants-1994_03
Patent number
US05298513

Reaction notes

Loading…