Hydrochloric Acid → N-(3-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride

HRID 35230Notes

Reaction equation

HRID 35230 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([O:23][CH3:24])[CH:19]=3)[CH:14]2[CH3:27])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].B.[ClH:29]>C1COCC1>[ClH:29].[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH2:10][CH2:11][N:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([O:23][CH3:24])[CH:19]=2)[CH:14]1[CH3:27])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14230297N-(3-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

Product 1

HCID 14230299N-(3-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (22.0 g, 0.059 m) was added portionwise to 190 ml of 1 M borane in THF which was maintained under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 15 minutes, then heated to reflux for 4 hours. The mixture was cooled in an ice bath, treated carefully with 20% HCl (250 ml), and then refluxed for 1 hour. After cooling, the solvents were removed on an aspirator and the residue treated with 250 ml 20% NaOH and extracted with chloroform (3×200 ml). The extracts were dried over MgSO6 and evaporated to an oily residue. The residue was dissolved in methanol (100 ml) and treated with HCl gas until acidic. Upon cooling, a yellow solid was obtained which was collected by filtration and dried to give 23.2 g N-(3-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride, m.p. 139°-140°.

Workup

  1. temperaturewas maintained under a nitrogen atmosphere
  2. temperatureheated
  3. temperatureto reflux for 4 hours
  4. temperatureThe mixture was cooled in an ice bath
  5. temperaturerefluxed for 1 hour
  6. temperatureAfter cooling
  7. customthe solvents were removed on an aspirator
  8. additionthe residue treated with 250 ml 20% NaOH
  9. extractionextracted with chloroform (3×200 ml)
  10. dry with materialThe extracts were dried over MgSO6
  11. customevaporated to an oily residue
  12. dissolutionThe residue was dissolved in methanol (100 ml)
  13. additiontreated with HCl gas until acidic
  14. temperatureUpon cooling
  15. customa yellow solid was obtained which
  16. filtrationwas collected by filtration
  17. customdried

Sources & evidence

ORD record
ord-244b101da21d455e87989b72a1190a60
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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