6-amino-3-(N-propionyl-N-n-propylamino)chroman → 6-Amino-3-(di-n-propylamino)chroman

HRID 1975765Notes

Reaction equation

HRID 1975765 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH:6]([N:12]([C:16](=O)[CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH:6]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:5]2

Participants

4

Reactant 2

HCID 105634506-amino-3-(N-propionyl-N-n-propylamino)chromanHCID 21226445Aluminium lithium hydride

Product 1

HCID 106105856-Amino-3-(di-n-propylamino)chromanYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-amino-3-(N-propionyl-N-n-propylamino)chroman (18) (300 mg, 1.03 mmol) in anhydrous diethyl ether was added LiAlH4 (300 mg, 7.89 mmol). The mixture was stirred for 1.5 hours at room temperature. Excess hydride was quenched by addition water (0.5 ml), 15% sodium hydroxide (0.3 ml) and water (0.9 ml). The mixture was filtered and the solvent evaporated yielding 216 mg (85%) of 23 as an oil.

Workup

  1. customExcess hydride was quenched by addition water (0.5 ml), 15% sodium hydroxide (0.3 ml) and water (0.9 ml)
  2. filtrationThe mixture was filtered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-84e3b95febe841afa3d8eec25caabdb4
Source dataset
uspto-grants-1994_02
Patent number
US05288748

Reaction notes

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