Aluminum(III) Chloride → 5-Benzyl-3b,4,5,6,7,7a-hexahydro-3-thia-5-aza-cyclopenta[alpha]inden-8-one

HRID 30275Notes

Reaction equation

HRID 30275 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](Cl)=[O:15])[CH:10]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH:11]([C:14](=[O:15])[C:21]3[CH:20]=[CH:19][S:18][C:17]=32)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 862290891-Benzyl-3-thiophen-2-yl-piperidine-4-carbonyl chloride

Product 1

HCID 597894175-Benzyl-3b,4,5,6,7,7a-hexahydro-3-thia-5-aza-cyclopenta[alpha]inden-8-oneYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from step d) (2.9 g, 8.15 mmol) in CH2Cl2 (12 ml) was added dropwise to a slurry of AlCl3 (3.26 g, 24.5 mmol) in CH2Cl2 (28 ml) at 220C. After 45 minutes, the reaction mixture was poured into ice cold 2 M NaOH (100 ml) and extracted with CH2Cl2 (300 ml). The organic extract was dried (MgSO4), solvent evaporated in vacuo, and residue purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 50% ethyl acetate) to give the subtitle compound (1.32 g, 57%). MS calculated for C17H17NOS+H 284, observed 284.

Workup

  1. extractionextracted with CH2Cl2 (300 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4), solvent
  4. customevaporated in vacuo, and residue
  5. custompurified by silica-gel chromatography

Sources & evidence

ORD record
ord-2aea481de6884d59b280f8b76106d7c1
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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