Water → HCID 22007050, compound

HRID 323713Notes

Reaction equation

HRID 323713 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[C:12]([N+:16]([O-])=O)[CH2:13][CH2:14][CH3:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH:12]([NH2:16])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 53993673HCID 53993673, compound

Product 1

HCID 22007050HCID 22007050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.70 g (31.9 mmol) of 1-(2-naphthyl)-2-nitro-1-pentene in tetrahydrofuran (THF) (30 ml) was added dropwise to a suspension of 2.42 g (63.8 mmol) of lithium aluminum hydride (LiAlR4) in THF (40 ml) over 1 hr under ice cooling and the mixture was stirred overnight at room temperature. After excessive LiAlH4 was decomposed with distilled water under ice cooling the mixture was filtered and the filtrate was concentrated. Thereafter, ether (100 ml) was added to the concentrate and was extracted three times with 0.5 N hydrochloric acid (50 ml). The obtained water phase was alkalized with 28% aqueous ammonia and was extracted three times with ether (100 ml). The obtained organic phase was dried over anhydrous sodium sulfate, concentrated and purified by flash column chromatography. A mixture of chloroform/methanol (10:1) was used for eluting solvent, 1-(2-naphthyl)-2-aminopentane was obtained to yield 5.36 g (79%) as light yellow oil.

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated
  3. additionThereafter, ether (100 ml) was added to the
  4. concentrationconcentrate
  5. extractionwas extracted three times with 0.5 N hydrochloric acid (50 ml)
  6. extractionwas extracted three times with ether (100 ml)
  7. dry with materialThe obtained organic phase was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by flash column chromatography
  10. additionA mixture of chloroform/methanol (10:1)
  11. washfor eluting solvent

Sources & evidence

ORD record
ord-b0d83dce9d0e411aacecc0e13f6a9526
Source dataset
uspto-grants-2001_04
Patent number
US06214859B1

Reaction notes

Loading…