Hydrochloric Acid → WAY-470

HRID 1882761Notes

Reaction equation

HRID 1882761 reaction equation
C([N:4]1[CH2:16][C:14]2=[C:15]3[C:10](=[CH:11][CH:12]=[CH:13]2)[C:9]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:8]=2[N:7]3[CH2:6][CH2:5]1)(=O)C.Cl>CO.[OH-].[Na+]>[CH2:6]1[N:7]2[C:15]3[C:10]([C:9]4[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:8]=42)=[CH:11][CH:12]=[CH:13][C:14]=3[CH2:16][NH:4][CH2:5]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23509582HCID 23509582, compound

Product 1

HCID 10037962WAY-470Yield 61.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
95 °C

Procedure

3-Acetyl-1,2,3,4,8,9,10,11,12,13-decahydrocycloocta[b][1,4]diazepino[6,7,1-hi]indole (1.3 g) was dissolved in methanol and diluted with 2.5N NaOH and excess solid NaOH was added. The solution was heated at 95° C. overnight. The volatiles were evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic phase was separated and evaporated and the residue was purified by chromatography on silica gel eluting with 3-4% methanol in methylene chloride to give a colorless oil. The oil was treated with 4 N HCl with stirring and warming. The precipitate that formed was isolated by filtration, triturated with ethanol, and allowed to stand overnight. A yellow solid was isolated by filtration and dried to give the hydrochloride salt of the title compound (683 mg), mp: 316-318° C.

Workup

  1. additionwas added
  2. customThe volatiles were evaporated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe organic phase was separated
  5. customevaporated
  6. customthe residue was purified by chromatography on silica gel eluting with 3-4% methanol in methylene chloride
  7. customto give a colorless oil
  8. temperaturewarming
  9. customThe precipitate that formed
  10. customwas isolated by filtration
  11. customtriturated with ethanol
  12. customA yellow solid was isolated by filtration
  13. customdried

Sources & evidence

ORD record
ord-cc17032307714c408f1eb297eb80ce3b
Source dataset
uspto-grants-2004_07
Patent number
US06759405B2

Reaction notes

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