Propionyl chloride → 3-(N-propionyl-N-n-propylamino)chroman

HRID 1975762Notes

Reaction equation

HRID 1975762 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH2:6]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12][CH2:11]1)[CH2:7][CH3:8]>C(Cl)Cl.[OH-].[Na+]>[C:1]([N:9]([CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12][CH2:11]1)[CH2:6][CH2:7][CH3:8])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 62324Propionyl chlorideHCID 195921083-(N-n-propylamino)chroman

Product 1

HCID 108481013-(N-propionyl-N-n-propylamino)chromanYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Propionyl chloride (2.8 g, 29 mmol) was added to a mixture of 15 (1.2 g, 6.4 mmol) in CH2Cl2 and 5% aqueous NaOH. The mixture was stirred for 30 min and separated. The organic layer was extracted with water, separated and dried (MgSO4). The crude product was chromatographed (SiO2) with light petroleum-ether (2:1) as eluant yielding 0.98 g (62%) of 3-(N-propionyl-N-n-propylamino)chroman (16).

Workup

  1. customseparated
  2. extractionThe organic layer was extracted with water
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. customThe crude product was chromatographed (SiO2) with light petroleum-ether (2:1) as eluant

Sources & evidence

ORD record
ord-102627aca7b4441bac4d72d68df5c88a
Source dataset
uspto-grants-1994_02
Patent number
US05288748

Reaction notes

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