Hydrochloric Acid → HCID 19888684, compound

HRID 654231Notes

Reaction equation

HRID 654231 reaction equation
[C:1]([C:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:13][CH3:14])[CH:4]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[ClH:22]>O1CCCC1.C(O)C>[ClH:22].[NH2:2][CH2:1][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:13][CH3:14])[CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10845215HCID 10845215, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19888684HCID 19888684, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the compound obtained in step (v) above (9.2 g, 0.05 mol) in anhydrous tetrahydrofuran (150 ml) is added dropwise to a mixture of lithium aluminum hydride (3.8 g, 0.1 mol) and anhydrous tetrahydrofuran (50 ml) under nitrogen atmosphere. The reaction mixture is heated to the reflux temperature for 4 hours, and then cooled. Water (40 ml) is added thereto and the reaction mixture is extracted with ethyl acetate (2×300 ml). The organic phase is dried over sodium sulfate, filtered and concentrated to dryness. The residue is then purified by flash chromatography eluting with methanol/ammonia 97/3. The hydrochloride is prepared by treating the thus obtained free base with HCl saturated isopropanol. The product of the title (9 g) is thus obtained; m.p.231°-232° C. (ethanol).

Workup

  1. temperatureThe reaction mixture is heated to the reflux temperature for 4 hours
  2. temperaturecooled
  3. extractionthe reaction mixture is extracted with ethyl acetate (2×300 ml)
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue is then purified by flash chromatography
  8. washeluting with methanol/ammonia 97/3
  9. customThe product of the title (9 g) is thus obtained

Sources & evidence

ORD record
ord-aef6b0f9aa364cf2aaaad9792680dfba
Source dataset
uspto-grants-1992_07
Patent number
US05130339

Reaction notes

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