Hydrochloric Acid → HCID 10292950, compound

HRID 992258Notes

Reaction equation

HRID 992258 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 x). The combined extracts are washed with H2O (2 x) 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 x)
  4. washThe combined extracts are washed with H2O (2 x) 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-d04e89c5a3484111b645c6b19ca358b5
Source dataset
uspto-grants-2002_10
Patent number
US06468999B1

Reaction notes

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