Benzyl Bromide → HCID 53995652, compound

HRID 981945Notes

Reaction equation

HRID 981945 reaction equation
[CH2:1]([CH:3]1[CH2:9][NH:8][C:7]2=[C:10]3[C:15](=[N:16][C:17]4=[CH:18][CH:19]=[CH:20][C:5](=[C:6]24)[O:4]1)[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH3:2].CC(C)([O-:24])C.[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[CH2:27]([N:8]1[C:7]2=[C:10]3[C:15](=[N:16][C:17]4=[CH:18][CH:19]=[CH:20][C:5](=[C:6]24)[O:4][CH:3]([CH2:1][CH3:2])[C:9]1=[O:24])[CH2:14][CH2:13][CH2:12][CH2:11]3)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 23665647Potassium tert-butoxideHCID 54017563HCID 54017563, compound

Product 1

HCID 53995652HCID 53995652, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-ethyl-2,3,9,10,11,12-hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepine (5.0 g) in dry tetrahydrofuran (150 ml) was added potassium t-butoxide (3.0 g). The mixture was stirred for 15 mins, benzyl bromide (3.16 ml) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was heated at reflux for 1.5 hrs, allowed to cool, concentrated and diluted with saturated sodium bicarbonate solution (250 ml). The mixture was extracted twice with ethyl acetate (250 ml), and the organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated. Trituration of the residue first with pentane and then diethyl ether, gave 4.65 g (71%) of 1-benzyl-3-ethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1.5 hrs
  4. temperatureto cool
  5. concentrationconcentrated
  6. additiondiluted with saturated sodium bicarbonate solution (250 ml)
  7. extractionThe mixture was extracted twice with ethyl acetate (250 ml)
  8. dry with materialthe organic extracts were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-aaefb72635c94730921a48a975e81633
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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