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

HRID 35233Notes

Reaction equation

HRID 35233 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([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)[CH2:14]2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].B.[ClH:28]>O1CCCC1>[ClH:28].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][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)[CH2:14]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 100895966,7-Dimethoxy-2-[(4-nitrophenyl)acetyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 14230287N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(4-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (28.45 g, 0.08 m) was added portionwise to a stirred solution of 1 M borane in tetrahydrofuran (320 ml, 0.32 m) which was diluted with 180 ml of dry tetrahydrofuran and maintained under nitrogen. The mixture was heated to reflux for 3 hours, then cooled in an ice bath and carefully treated with 100 ml of 20% HCl. The mixture was heated to reflux for 1 hour, then allowed to cool. The solvent was removed at an aspirator (40°) and the residue slurried with cold water (400 ml) and the solid collected by filtration, washed with water and air dried. The hydrochloride salt was prepared in 300 ml of a methanol, isopropanol, ether mixture and dried to give 18.0 g N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride, m.p. 154°-155°.

Workup

  1. temperaturemaintained under nitrogen
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 3 hours
  4. temperaturecooled in an ice bath
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 1 hour
  7. temperatureto cool
  8. customThe solvent was removed at an aspirator (40°)
  9. filtrationthe residue slurried with cold water (400 ml) and the solid collected by filtration
  10. washwashed with water and air
  11. customdried
  12. dry with materialisopropanol, ether mixture and dried

Sources & evidence

ORD record
ord-6fe12898c1d14edb9a0f623174eacc70
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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