Borane;tetrahydrofuran → N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

HRID 35238Notes

Reaction equation

HRID 35238 reaction equation
B.C1COCC1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29][CH3:30])[CH:25]=3)[CH:20]2[CH3:31])=O)=[CH:12][CH:11]=1)([O-:9])=[O:8]>Cl>[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29][CH3:30])[CH:25]=3)[CH:20]2[CH3:31])=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 14230284N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline

Product 1

HCID 14230288N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinolineYield 77.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 200 ml of 0.5 M borane/THF was treated with N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline (11.5 g, 0.03 m) portionwise, at room temperature, then warmed to reflux. After 30 min at reflux, the reaction was cooled and acidified with 60 ml of 20% HCl, added dropwise. The acidified reaction mixture was refluxed one hour, then concentrated on the rotovap at 40° C. to about 1/3 volume, then diluted with 600 ml water. The mixture was basified, then extracted with CH2Cl2 (2×400 ml). The CH2Cl2 was concentrated to an oil which crystallized when treated with 200 ml ether. The product was filtered off and air dried, giving 8.5 g N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline, m.p. 176°-178° (86%).

Workup

  1. temperatureAfter 30 min at reflux
  2. temperaturethe reaction was cooled
  3. additionadded dropwise
  4. customThe acidified reaction mixture
  5. temperaturewas refluxed one hour
  6. concentrationconcentrated on the rotovap at 40° C. to about 1/3 volume
  7. additiondiluted with 600 ml water
  8. extractionextracted with CH2Cl2 (2×400 ml)
  9. concentrationThe CH2Cl2 was concentrated to an oil which
  10. customcrystallized when
  11. additiontreated with 200 ml ether
  12. filtrationThe product was filtered off
  13. customair dried

Sources & evidence

ORD record
ord-ac22341d1d944aae934aba240c2016aa
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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