Benzothiazole → HCID 54135947, compound

HRID 1738895Notes

Reaction equation

HRID 1738895 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([N-]C(C)C)(C)C.[Li+].[C:18]1([CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([CH:31]=[CH:32][CH:33]=[O:34])[CH2:27][CH2:26]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.C1CCCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:33]([OH:34])[CH:32]=[CH:31][CH:28]1[CH2:27][CH2:26][N:25]([CH2:24][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 7222BenzothiazoleHCID 2724682Lithium diisopropylamideHCID 54371753HCID 54371753, compound

Product 1

HCID 54135947HCID 54135947, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

A solution of benzothiazole (0.243 g, 1.8 mmol) in 5 ml of dry THF was treated with 1.5 M lithium diisopropylamide in cyclohexane (1.45 ml) at -78° C. and stirred at that temperature for 15 minutes. A solution of 3-[1-(phenyl-methyl)-4-piperidinyl]propenal (452 mg, 1.97 mmol) in 3 ml of dry THF was added at -78° C. and stirred at that temperature for 30 minutes. The mixture was quenched with water and extracted with chloroform. The organic layer was dried and concentrated to give a thick yellow oil in a quantitative yield.

Workup

  1. stirringstirred at that temperature for 30 minutes
  2. customThe mixture was quenched with water
  3. extractionextracted with chloroform
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customto give a thick yellow oil in a quantitative yield

Sources & evidence

ORD record
ord-a3b3369d190547898d6ae82685e18cab
Source dataset
uspto-grants-1999_10
Patent number
US05965574

Reaction notes

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