Hydrochloric Acid → HCID 20058353, compound

HRID 2050482Notes

Reaction equation

HRID 2050482 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10](=O)[CH2:11][C:12]1[N:13]([CH3:21])[C:14]3[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:2]2.B.Cl.[OH-].[Na+].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1COCC1.C(OCC)(=O)C.CO>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([NH:9][CH2:10][CH2:11][C:12]1[N:13]([CH3:21])[C:14]3[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:2]2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 20058356HCID 20058356, compound

Product 1

HCID 20058353HCID 20058353, compoundYield 26.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(1-azabicyclo[2.2.2]oct-3-yl)-1-methyl-1H-indole 2-acetamide (1.4 g) in dry THF (30 ml) under nitrogen was added borane (1M solution in THF; 30 ml), and the mixture was heated under reflux for 3 h and then cooled in ice. Methanol (10 ml) was added dropwise followed by 5M hydrochloric acid (50 ml), and the mixture was then heated at reflux for 4 h. The cooled solution was poured into 2M sodium hydroxide solution (200 ml), and the mixture was extracted with ethyl acetate (2x200 ml). The combined, dried organic extracts were evaporated in vacuo to give an oil which was dissolved in dry THF (45 ml). 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (1.13 g) was added slowly in small portions over 15-20 min and the resulting suspension was stirred for 30 min. The mixture was diluted with ethyl acetate (250 ml) and washed with 2M sodium hydroxide solution (2x250 ml). The organic layer was dried and evaporated in vacuo to give a gum which was purified by FCC eluting with System A (75:8:1) to give the title compound (354 mg) as an oil, t.l.c. (System A,75:8:1) Rf 0.24.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. temperaturecooled in ice
  4. temperaturethe mixture was then heated
  5. temperatureat reflux for 4 h
  6. extractionthe mixture was extracted with ethyl acetate (2x200 ml)
  7. customdried organic extracts were evaporated in vacuo
  8. customto give an oil which
  9. washwashed with 2M sodium hydroxide solution (2x250 ml)
  10. customThe organic layer was dried
  11. customevaporated in vacuo
  12. customto give a gum which
  13. customwas purified by FCC
  14. washeluting with System A (75:8:1)

Sources & evidence

ORD record
ord-36b48505867745298631197c3eeab1e7
Source dataset
uspto-grants-1991_05
Patent number
US05013733

Reaction notes

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