Hydrochloric Acid → HCID 13446113, compound

HRID 1277931Notes

Reaction equation

HRID 1277931 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:9][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4]1.[Li].C([BH-](C(CC)C)C(CC)C)(CC)C.Cl>C1(C)C=CC=CC=1.CCCCCC.O1CCCC1>[CH3:1][NH:2][CH:3]1[CH2:9][CH:8]([OH:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 134460763-(Methylamino)-3,4-dihydro-1-benzoxepin-5(2H)-oneHCID 131712294HCID 131712294, compound

Product 1

HCID 13446113HCID 13446113, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a boiling solution of 80 g (0.5 mole) rac.-3-methylamino-3,4-dihydro-1-benzoxepin-5-(2H)-one in a mixture of 550 ml toluene and 300 ml hexane, 550 ml of a 1 molar solution of lithium-tri-sec.-butylborohydride in tetrahydrofuran are added in drops, so that the solution is maintained boiling. Following the completion of the addition, the mixture is heated to boiling for another hour. After cooling, the mixture is acidified by the drop-wise addition of methanolic hydrochloric acid. The methanol phase is then separated and the toluene/hexane mixture is again extracted with hydrochloric acid in methanol. The extracts are evaporated, taken up with dichloromethane and a solution (10%) of sodium carbonate, the organic phase washed with saturated sodium chloride, dried over sodium sulfate and evaporated to dryness. 67.6 g (70% of the theoretical yield) of rac.-2,3,4,5-tetrahydro-3-methylamino-1-benzoxepin-5-ol are obtained in the form of an oily residue, wherein rac.-cis-2,3,4,5-tetrahydro-3-methylamino-1-benzoxepin-5-ol predominates with 82 parts for 18 parts of rac.-trans-2,3,4,5 -tetrahydro-3-methylamino-1-benzoxepin-5-ol. The compounds may be separated and identified as described hereinabove.

Workup

  1. additionare added in drops, so that the solution
  2. temperatureis maintained
  3. additionthe completion of the addition
  4. temperaturethe mixture is heated
  5. waitto boiling for another hour
  6. temperatureAfter cooling
  7. customThe methanol phase is then separated
  8. extractionthe toluene/hexane mixture is again extracted with hydrochloric acid in methanol
  9. customThe extracts are evaporated
  10. washa solution (10%) of sodium carbonate, the organic phase washed with saturated sodium chloride
  11. dry with materialdried over sodium sulfate
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-3f7e7901401946ce9019929af75408f7
Source dataset
uspto-grants-1981_07
Patent number
US04279904

Reaction notes

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