Dimethylformamide → 1-Benzyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,2]benzoxazepin-2-one

HRID 981928Notes

Reaction equation

HRID 981928 reaction equation
N1[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]CC1=O)[CH2:12][CH2:11][CH2:10][CH2:9]3.[CH3:20][C:21](C)([O-:23])C.[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C[N:35](C)C=O>O>[CH2:26]([CH:20]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][NH:35][C:21]1=[O:23])[CH2:12][CH2:11][CH2:10][CH2:9]3)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 9795016HCID 9795016, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 200686091-Benzyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,2]benzoxazepin-2-oneYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.30 g) in dry dimethylformamide (50 ml) was added potassium tert-butoxide (2.1 g). To the solution was added benzyl bromide (2.22 ml), and stirring was continued for five mins. The reaction mixture was diluted with water (150 ml) and extracted with diethyl ether. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. Trituration of the residue with pentane followed by recrystallization from methanol gave 2.42 g (41%) of product, mp 166°-167.5° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customTrituration of the residue with pentane followed by recrystallization from methanol

Sources & evidence

ORD record
ord-52eddcb74c254b0784d88f87ed38dc13
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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