Hydrochloric Acid → (S)-7-Chloro-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochloride

HRID 131480Notes

Reaction equation

HRID 131480 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[NH:6][C:7]3[S:8][C:9]([CH3:25])=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[C@@H:16]([CH2:21][CH2:22][O:23][CH3:24])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1.[ClH:28]>CC(O)C>[ClH:1].[ClH:28].[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[NH:6][C:7]3[S:8][C:9]([CH3:25])=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[C@@H:16]([CH2:21][CH2:22][O:23][CH3:24])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136090349(S)-7-Chloro-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Product 1

HCID 136384340(S)-7-Chloro-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochlorideYield 199.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
79.5 °C

Procedure

Combine (S)-7-chloro-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (39.7 g, 97.6 mmol) and 2-propanol (IPA, 397 mL) at ambient temperature and hear to 80-81° C. Add a solution of concentrated HCl (17.1 mL, 206 mmol) in IPA (79 mL) over 20-30 minutes. Maintain the temperature of the resulting mixture at 79-80° C. for 1.5 hours. Shut heat source and allow the mixture to cool slowly to 30° C. over 3 hours. Cool to 0-5° C. and stir for an additional hour. Filter the solids and rinse with ice cold IPA (3×50 mL). Dry at 50° C. to afford 46.5 g (99.3%) of the title compound. KF analysis gives 5.47% H2O, Chloride analysis affords a value of 12.8%.

Workup

  1. customat ambient temperature
  2. customhear to 80-81° C
  3. temperatureShut heat source
  4. temperatureto cool slowly to 30° C. over 3 hours
  5. temperatureCool to 0-5° C.
  6. filtrationFilter the solids
  7. washrinse with ice cold IPA (3×50 mL)
  8. customDry at 50° C.

Sources & evidence

ORD record
ord-d5387801b4f942d2957ec75505bec2b3
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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