Potassium Hydroxide → Ihch-7113

HRID 1789962Notes

Reaction equation

HRID 1789962 reaction equation
[OH-].[K+].[CH3:3][N:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[C@@H:14]4[CH2:19][N:18](C(OCC)=O)[CH2:17][CH2:16][C@@H:15]4[N:7]([C:8]=23)[CH2:6][CH2:5]1>C(O)CCC>[CH3:3][N:4]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]3[C@@H:14]4[CH2:19][NH:18][CH2:17][CH2:16][C@@H:15]4[N:7]([C:8]=23)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21302624Ethyl (6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido(3',4':4,5)pyrrolo(1,2,3-de)quinoxaline-8(7H)-carboxylate

Product 1

HCID 21302499Ihch-7113Yield 95.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Powdered potassium hydroxide (10.0 g) was added to a stirred solution of ethyl (6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.52 g, 15.0 mmol) in warm 1-butanol (50 mL) and the resulting mixture was heated under reflux for 5 h. It was then evaporated under reduced pressure and the residue treated with water and extracted with dichloromethane (2×). The extract was washed with water, dried over magnesium sulfate and concentrated to yield 3.27 g (95%) of the title compound as a viscous liquid. 1H NMR (CDCl3, 300 MHz) δ 1.74–1.93 (m, 4H), 2.57–2.71 (m, 1H), 2.80–2.95 (m, 3H), 2.87 (s, 3H), 2.95–3.12 (m, 2H), 3.26–3.38 (m, 3H), 3.55–3.64 (m, 1H), 6.41 (d, J=7.3 Hz, 1H), 6.51 (d, J=7.3 Hz, 1H), 6.65 (t, J=7.3 Hz, 1H) ppm. MS (CI): 230 (M+H+).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 h
  3. customIt was then evaporated under reduced pressure
  4. additionthe residue treated with water
  5. extractionextracted with dichloromethane (2×)
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-46d7f2d51615421183cda533e5cd96d7
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

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