Hydrochloric Acid → 6-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride

HRID 1013095Notes

Reaction equation

HRID 1013095 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[ClH:14].CCCCCCC>C(O)C>[ClH:14].[CH3:1][O:2][C:3]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8900HeptaneHCID 138533586-Methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 574580206-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochlorideYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Dissolve crude 6-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (35.1 g, 0.198 mol) in ethanol (250 mL). Heat the solution to reflux and add 2 N HCl in ethanol (108.9 mL, 0.218 mol, 1.1 equiv.). Slowly add heptane (700 mL) over 10 min, then remove the heating mantle and cool the solution to RT and finally continue the cooling with an ice water mixture. Collect the resulting solid by vacuum filtration and wash with cold 1:2 ethanol:heptane (3×100 mL), dry for 15 min while applying vacuum suction, then further dry the product in a vacuum oven at 60° C. for 1 h to give the title compound as a white granular solid (35.53 g, 63%).

Workup

  1. temperatureHeat the solution
  2. temperatureto reflux
  3. customremove the heating mantle
  4. customCollect the resulting solid
  5. filtrationby vacuum filtration
  6. washwash with cold 1:2 ethanol
  7. dry with materialheptane (3×100 mL), dry for 15 min
  8. customfurther dry the product in a vacuum oven at 60° C. for 1 h

Sources & evidence

ORD record
ord-42bd5e048db744538c1c8ac5a40e90de
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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