Water → HCID 18434222, compound

HRID 1636732Notes

Reaction equation

HRID 1636732 reaction equation
[CH2:1]([N:4]([CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:2]=[CH2:3].[H-].[Na+].Cl[C:16]1[N:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1.O>C1COCC1>[CH2:1]([N:4]([CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:16]1[N:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 10877584HCID 10877584, compound

Product 1

HCID 18434222HCID 18434222, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

490 mg of 6-(allyl-methyl-amino)-hexan-1-ol (Ex. 42.B) in 5 ml of THF are treated over a period of 1.5 h. with 240 mg of NaH (55-60% dispersion in mineral oil) and with 410 mg of 1-(6-chloro-pyridin-3-yl)-ethanone (Ex. 42.D.a) in 4 ml of THF. The solution is stirred at RT, treated with water and filtered and the residue is washed with methylene chloride. The phases are separated and the inorganic phase is extracted with methylene chloride and then with ethyl acetate. The organic phases are concentrated, taken up in methylene chloride and extracted with 1M HCl. The acidic-aqueous phase is washed with methylene chloride, made basic with NaOH and extracted with methylene chloride. The organic phase is washed with NaHCO3 solution and saturated sodium chloride solution and dried. The crude product is purified on silica gel with methylene chloride:methanol (9:1). 177.8 mg of 1-[6-[6-(allyl-methyl-amino)-hexyloxy]-pyridin-3-yl]-ethanone are obtained as an oil. 176.4 mg of this are converted with 70 mg of fumaric acid into 1-[6-[6-(allyl-methyl-amino)-hexyloxy]pyridin-3-yl]-ethanone.fumarate (1:1), MS: m/e 291 (M+H+).

Workup

  1. filtrationfiltered
  2. washthe residue is washed with methylene chloride
  3. customThe phases are separated
  4. extractionthe inorganic phase is extracted with methylene chloride
  5. concentrationThe organic phases are concentrated
  6. extractionextracted with 1M HCl
  7. washThe acidic-aqueous phase is washed with methylene chloride
  8. extractionextracted with methylene chloride
  9. washThe organic phase is washed with NaHCO3 solution and saturated sodium chloride solution
  10. customdried
  11. customThe crude product is purified on silica gel with methylene chloride:methanol (9:1)

Sources & evidence

ORD record
ord-e96276e5b8a44d69b19b9833a848b410
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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