1,2-Dichloroethane → 8-Bromo-3-(n-propylamino)chroman

HRID 1464700Notes

Reaction equation

HRID 1464700 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]([NH2:12])[CH2:7]2.[C:13](Cl)(=O)[CH2:14][CH3:15].[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCCl>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]([NH:12][CH2:13][CH2:14][CH3:15])[CH2:7]2

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 62324Propionyl chlorideHCID 169536Tetrabutylammonium borohydrideHCID 162444248-Bromo-3,4-dihydro-2H-1-benzopyran-3-amine

Product 1

HCID 190871638-Bromo-3-(n-propylamino)chromanYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

To a mixture of 8-bromo-3-aminochroman (200 mg; 0.9 mmol) in CH2Cl2 (25 ml) and 10% aqueous Na2CO3 (25 ml) was added propionyl chloride (400 mg; 2.2 mmol) and the mixture was stirred for 2 hours. The phases were separated and the organic layer was dried (MgSO4). The solvent was evaporated and the crude amide was reduced with tetrabutylammonium borohydride (400 mg, 1.6 mmol) in a boiling (1:1)-mixture (50 ml) of dichloromethane and 1,2-dichloroethane overnight. The solution was extracted with water, dried (Na2SO4) and the solvent was evaporated yielding 140 mg (58%) of 8-bromo-3-(n-propylamino)chroman.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customThe solvent was evaporated
  4. extractionThe solution was extracted with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2b8f1eb86b624f778728c4485e55527b
Source dataset
uspto-grants-1994_04
Patent number
US05306830

Reaction notes

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