Tetrahydrofuran → 1-(6-Chlorobenzo[b]thien-3-yl)-piperazine

HRID 2392579Notes

Reaction equation

HRID 2392579 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[CH:8][S:7](=O)(=O)[C:6]=2[CH:18]=1.O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[H][H]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)=[CH:8][S:7][C:6]=2[CH:18]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 70199140HCID 70199140, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 155414601-(6-Chlorobenzo[b]thien-3-yl)-piperazineYield 111.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 6-chloro-3-piperazinyl-benzo[b]thiophene-1,1-dioxide (6.0 g) and tetrahydrofuran (THF) (30 mL) under a nitrogen atmosphere was added a solution of D1BAL-H (diisobutylaluminum hydride) (0.084 mol) in toluene (84 mL) dropwise with ice bath cooling. The reaction mixture was stirred at 0° C. for 2 hours then overnight at room temperature. To the yellow solution was added, with vigorous stirring, water (5 ml) at a rate to control hydrogen evolution. Then 5NNaOH (5 mL) was added with rapid stirring. The resulting precipitate was filtered off and washed with dichloromethane and ether. The filtrate was concentrated in vacuo. The residue was taken up in dichloromethane (150 mL), washed with water (75 mnl) and brine (100 ml), dried over sodium sulfate and concentrated in vacuo to yield 5.93 g of a viscous gummy material which was triturated with ether. The ether fraction was concentrated in vacuo to yield 2.75 g of residue which was chromatographed (silica gel, 50% MeOH/CH2 Cl2) to yield 1.53 g product as a clear oil.

Workup

  1. temperaturecooling
  2. customovernight
  3. customat room temperature
  4. addition(5 mL) was added with rapid stirring
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with dichloromethane and ether
  7. concentrationThe filtrate was concentrated in vacuo
  8. washwashed with water (75 mnl) and brine (100 ml)
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9eac1c28d2644b86965636be8b717436
Source dataset
uspto-grants-1998_09
Patent number
US05801176

Reaction notes

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