Hydrochloric Acid → HCID 19821577, compound

HRID 979237Notes

Reaction equation

HRID 979237 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])C1C=CC=CC=1.[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26].[OH-:27].[Na+].Cl>[Pd].CO>[OH:27][C:14]1[C:9](=[O:8])[CH:10]=[CH:16][N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]2[CH:12]=[CH:13][C:14](=[O:15])[C:9]([OH:8])=[C:10]2[CH3:16])[C:13]=1[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 242501,8-OctanediamineHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 19821577HCID 19821577, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

3-Benzyloxy-2-methyl-4-pyrone (0.066 moles) and 1,8-diaminooctane (0.022 moles) are mixed in 2:1 v/v aqueous methanol (300 ml), solid sodium hydroxide (2 g) is added, and the mixture is heated on a steam bath for 5 hours. The mixture is allowed to cool and an aliquot is taken, acidified to pH 2 with concentrated hydrochloric acid and the solvent removed on the rotary evaporator to give a solid residue. This residue is checked for completion of the reaction through its n.m.r. spectrum, the presence of protons exchangeable at ca δ=8.3 (d6DMSO) showing that the reaction is not complete. If this is the case, refluxing is continued until the solid obtained from an aliquot shows no such protons. On complete reaction being found to have occurred, the mixture is cooled and acidified to pH 2 with concentrated hydrochloric acid, any precipitate formed at this stage being dissolved by the addition of methanol to the mixture. Palladium/carbon catalyst is then added and the solution is hydrogenated at room temperature and atmospheric pressure in order to effect debenzylation. The catalyst is removed by filtration and the solvent by rotary evaporation, the resulting solid then being recrystallised from water to give the title compound(1) in 40% yield as a white solid of m.p. 297°-300° dec; γmax (nujol) 1340 and 1620 cm-1 ; δ(d6DMSO/D2O), 1.5 (m, 12H), 2.5 (s, 6H), 4.3 (m, 4H), 7.1 (d, 2H) and 8.1 (d, 2H); m/e 360.

Workup

  1. additionis added
  2. temperaturethe mixture is heated on a steam bath for 5 hours
  3. temperatureto cool
  4. customthe solvent removed on the rotary evaporator
  5. customto give a solid residue
  6. customThis residue is checked for completion of the reaction through its n.m.r
  7. temperaturerefluxing
  8. customobtained from an aliquot
  9. customOn complete reaction
  10. temperaturethe mixture is cooled
  11. customany precipitate formed at this stage
  12. customis hydrogenated at room temperature
  13. customThe catalyst is removed by filtration
  14. customthe solvent by rotary evaporation
  15. customthe resulting solid then being recrystallised from water
  16. customto give the title compound(1) in 40% yield as a white solid of m.p. 297°-300° dec

Sources & evidence

ORD record
ord-778ca581211747b783a101189497bf1c
Source dataset
uspto-grants-1987_05
Patent number
US04666927

Reaction notes

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