Tetrahydrofuran → HCID 178457166, compound

HRID 848441Notes

Reaction equation

HRID 848441 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[N:3]=1.[CH:9]([N:12]=[CH:13]C)([CH3:11])[CH3:10].[Cl-].[NH4+].O1CCC[CH2:18]1>C([Li])CCC.CCCCCC>[OH:8][C:4]1[N:3]=[C:2]([CH:1]([CH3:18])[CH2:13][NH:12][CH:9]([CH3:11])[CH3:10])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 141371(E)-N-IsopropylacetaldimineHCID 178425782HCID 178425782, compound

Product 1

HCID 178457166HCID 178457166, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 178418339ButyllithiumSolvent

Procedure

To the solution of 10.9 g of 2-methyl-6-hydroxypyridine in 400 ml of tetrahydrofuran, 88 ml of 2.5 molar n-butyllithium in hexane are added dropwise while stirring under nitrogen at 0°. After 2 hours 10.2 g of 1-isopropyliminoethane are added rapidly and the mixture stirred for 2 hours at 0°. It is poured into 200 ml of saturated aqueous ammonium chloride, the organic layer separated and the aqueous solution extracted 4 times with 150 ml of methylene chloride. The combined organic solutions are dried, filtered, evaporated and the residue is chromatographed on 300 g of silica gel with methanoldiethyl ether (5:1) as moving phase. The eluate is evaporated, the residue taken up in ethanol, neutralized with ethanolic fumaric acid and the resulting precipitate recrystallized from ethanol, to yield the mono-fumarate of N-[2-(6-hydroxy-2-pyridyl)propyl]-isopropylamine of Formula II, with R=OH, R'=H and CpH2p±1 =CH(CH3)2, melting at 193.5°-194°.

Workup

  1. stirringthe mixture stirred for 2 hours at 0°
  2. customthe organic layer separated
  3. extractionthe aqueous solution extracted 4 times with 150 ml of methylene chloride
  4. customThe combined organic solutions are dried
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue is chromatographed on 300 g of silica gel with methanoldiethyl ether (5:1)
  8. customThe eluate is evaporated
  9. customthe resulting precipitate recrystallized from ethanol

Sources & evidence

ORD record
ord-094c050556ba452faba2d44caf35f005
Source dataset
uspto-grants-1981_10
Patent number
US04296115

Reaction notes

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