Hydrochloric Acid → 2,3,9,10,11,12-Hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepine hydrochloride

HRID 981923Notes

Reaction equation

HRID 981923 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)[CH2:12][CH2:11][CH2:10][CH2:9]3.B.O1CCCC1.[ClH:26].[H][H]>O1CCCC1>[ClH:26].[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][CH2:2]1)[CH2:12][CH2:11][CH2:10][CH2:9]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuran2×HCID 9795016HCID 9795016, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 677565202,3,9,10,11,12-Hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepine hydrochlorideYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,3,9,10,11,12-Hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.00 g) was suspended in dry tetrahydrofuran (100 ml) and 1M borane/tetrahydrofuran (16.0 ml) was added. After 2 hrs, an additional 30 ml of 1M borane/tetrahydrofuran was added, and the reaction mixture was stirred overnight. The reaction mixture was poured into 5% hydrochloric acid and stirred unit hydrogen evolution ceased. The organic layer was separated and the aqueous phase was washed once with ethyl acetate. The aqueous phase was basified with 10% sodium hydroxide solution and precipitate was collected. The precipitate was treated with methanol/ether/hydrogen chloride. Recrystallized from methanol/ether gave 2.50 g (57.5%) of product, mp 300° C. (dec).

Workup

  1. customThe organic layer was separated
  2. washthe aqueous phase was washed once with ethyl acetate
  3. customwas collected
  4. additionThe precipitate was treated with methanol/ether/hydrogen chloride
  5. customRecrystallized from methanol/ether

Sources & evidence

ORD record
ord-eb4f3195a2f041bcb7a498caac08f820
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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