1-Bromopropane → HCID 53716832, compound

HRID 1195768Notes

Reaction equation

HRID 1195768 reaction equation
[NH:1]1[C:7]2=[C:8]3[C:13](=[N:14][C:15]4=[CH:16][CH:17]=[CH:18][C:5](=[C:6]24)[O:4][CH2:3][C:2]1=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9]3.[CH3:20][C:21](C)([O-])[CH3:22].[K+].BrCCC>O1CCCC1>[CH2:20]([N:1]1[C:7]2=[C:8]3[C:13](=[N:14][C:15]4=[CH:16][CH:17]=[CH:18][C:5](=[C:6]24)[O:4][CH2:3][C:2]1=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 9795016HCID 9795016, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 53716832HCID 53716832, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.94 g) in dry tetrahydrofuran (150 ml) was added potassium tert-butoxide (2.62 g). The mixture was stirred for 15 mins, 1-bromopropane (7.07 ml) was added, and the reaction mixture was refluxed overnight. The reaction mixture was concentrated, diluted with saturated potassium carbonate solution, and extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was to adhered to silica, and flash chromatographed (30% ethyl acetate/hexane). The appropriate fractions were evaporated and the residue was triturated with diethyl ether to yield 4.39 g (76%) of 1,3,9,10,11,12-hexahydro-1-propyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with saturated potassium carbonate solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customchromatographed (30% ethyl acetate/hexane)
  9. customThe appropriate fractions were evaporated
  10. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-d14a6c3c111346de93bb3b309bd91ff3
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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