Piperazine → 8-Chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzothiepino[4,3-b]pyridine

HRID 1647252Notes

Reaction equation

HRID 1647252 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6](Cl)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3

Participants

5

Reactant 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 15280235HCID 15280235, compound

Product 1

HCID 157805018-Chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzothiepino[4,3-b]pyridineYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of 8,11-dichloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridine (8.15 g, 0.029 mol) in tetrahydrofuran (100 mL) to a stirred suspension of piperazine (28.9 g, 0.34 mol) in tetrahydrofuran (290 mL) at 18°-19° C. over 20 minutes. Stir the mixture for 4 hours at room temperature and then pour it into 2.5M aqueous NaOH (250 mL) containing ice. Separate the layers, and extract the aqueous portion with EtOAc (3×100 mL). Combine the organic portions, and wash with H2O (3×75 mL) and brine (150 mL). Dry the mixture over MgSO4, filter, and concentrate the organic layer in vacuo to obtain the crude product (8.9 g). Purify the crude product via flash chromatography (9:1:0.125 CH2Cl2 /MeOH/NH4OH) to obtain the title compound (7.6 g, 78% yield).

Workup

  1. additioncontaining ice
  2. customSeparate the layers
  3. extractionextract the aqueous portion with EtOAc (3×100 mL)
  4. washCombine the organic portions, and wash with H2O (3×75 mL) and brine (150 mL)
  5. dry with materialDry the mixture over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate the organic layer in vacuo
  8. customto obtain the crude product (8.9 g)
  9. customPurify the crude product via flash chromatography (9:1:0.125 CH2Cl2 /MeOH/NH4OH)

Sources & evidence

ORD record
ord-7b179e8ebc574687b8530206fafb0149
Source dataset
uspto-grants-1995_07
Patent number
US05430032

Reaction notes

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