Hydrochloric Acid → HCID 10292950, compound

HRID 897159Notes

Reaction equation

HRID 897159 reaction equation
C([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[C:17]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:25])=[O:24])[CH:16]=[CH:15][C:14]=3[N:13]([CH3:32])[C:12]=2[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+].[ClH:35]>C(O)CO.O.C(Cl)Cl.CO>[ClH:35].[CH3:32][N:13]1[C:14]2[CH:15]=[CH:16][C:17]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:24])=[O:25])=[CH:18][C:19]=2[C:20]2[CH2:21][CH2:22][NH:9][CH2:10][CH2:11][C:12]1=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 12011168HCID 12011168, compound

Product 1

HCID 10292950HCID 10292950, compound

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 3-benzoyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (Step III, 1.25 g, 2.81 mmol) and potassium hydroxide (1.58 g, 28.1 mmol) in ethylene glycol (30 mL) is heated at 130° under nitrogen for 92 hr. Upon cooling, the mixture is diluted with H2O and extracted into ethyl acetate (3×). The combined extracts are washed with H2O (2×) and saline, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give a solid. The solid is dissolved in hot methylene chloride/methanol and treated with methanolic hydrochloric acid. The resultant mixture is concentrated and crystallized from ethyl acetate/methanol to give the title compound, mp>300°; IR (drift) 2820, 2792, 2747, 2717, 2704, 2665, 2651, 1299, 1147, 1096, 803, 729, 687, 643 and 621 cm−1; NMR (300 MHz, DMSO-d6) 9.41, 8.13, 7.85-7.95, 7.50-7.65, 3.70 and 3.10-3.40 δ; MS (EI) m/z 340 (M+), 298, 157, 156, 128, 78, 74, 73, 58 and 57; HRMS (FAB) calculated for C19H21N2O2S=341.1324, found=341.1319.

Workup

  1. temperatureis heated at 130° under nitrogen for 92 hr
  2. temperatureUpon cooling
  3. extractionextracted into ethyl acetate (3×)
  4. washThe combined extracts are washed with H2O (2×) and saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a solid
  9. concentrationThe resultant mixture is concentrated
  10. customcrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-5bb7de8a4e9746fd8713d9287a3a1dc8
Source dataset
uspto-grants-2005_07
Patent number
US06921823B2

Reaction notes

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