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

HRID 35225Notes

Reaction equation

HRID 35225 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](OC)=[C:18](OC)[CH:19]=3)[CH:14]2[CH3:27])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].B.[ClH:29]>C1COCC1>[ClH:29].[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][CH:17]=[CH:18][CH:19]=3)[CH:14]2[CH3:27])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14230283N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

Product 1

HCID 21295817N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-1-methylisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(4-Nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7- dimethoxy-1-methylisoquinoline (62.9 g, 0.17 m) was added portionwise to 500 ml of 1 M borane in THF which was diluted with 500 ml THF and maintained under nitrogen. The mixture was stirred at ambient temperature for 1 hr, then heated to reflux for 4 hr. The mixture was then cooled in an ice bath and treated carefully with 20% HCl (250 ml). The mixture was refluxed for 1 hr, cooled and then the solvents evaporated on an aspirator. Water (1 liter) was added and the solution basified to pH 11 with 50% NaOH, then extracted with CHCl3 (3×300 ml). The extracts were dried over MgSO4 and evaporated to an oily residue. The residue was dissolved in 300 ml of 1:1 methanol:isopropanol and treated with HCl gas until acidic. Upon cooling, a yellow solid was obtained which was collected by filtration and air dried to give 66.4 g (100+%) N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-1-methylisoquinoline hydrochloride. The product was slightly wet with isopropanol.

Workup

  1. temperaturemaintained under nitrogen
  2. temperatureheated
  3. temperatureto reflux for 4 hr
  4. temperatureThe mixture was then cooled in an ice bath
  5. temperatureThe mixture was refluxed for 1 hr
  6. temperaturecooled
  7. customthe solvents evaporated on an aspirator
  8. additionWater (1 liter) was added
  9. extractionextracted with CHCl3 (3×300 ml)
  10. dry with materialThe extracts were dried over MgSO4
  11. customevaporated to an oily residue
  12. dissolutionThe residue was dissolved in 300 ml of 1:1 methanol
  13. additionisopropanol and treated with HCl gas until acidic
  14. temperatureUpon cooling
  15. customa yellow solid was obtained which
  16. filtrationwas collected by filtration and air
  17. customdried

Sources & evidence

ORD record
ord-dda17c86dc5c49ae81000db830bc5291
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

Loading…