Aluminum(III) Chloride → 6-Benzyl-3b,4,5,6,7,7a-hexahydro-1-thia-6-aza-cyclopenta[alpha]inden-8-one

HRID 1013387Notes

Reaction equation

HRID 1013387 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:10]([C:19](Cl)=[O:20])[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[CH2:13][CH2:12][CH:11]2[CH:10]([C:19](=[O:20])[C:15]3[S:16][CH:17]=[CH:18][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 862292151-Benzyl-4-thiophen-3-yl-piperidine-3-carbonyl chloride

Product 1

HCID 597894296-Benzyl-3b,4,5,6,7,7a-hexahydro-1-thia-6-aza-cyclopenta[alpha]inden-8-oneYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from step e) (4.38 g, 12.3 mmol) in CH2Cl2 (18.5 ml) was added dropwise to a slurry of AlCl3 (4.91 g, 36.9 mmol) in CH2Cl2 (42 ml) at 22° C. 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) and purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 50% ethyl acetate) to give the subtitle product (434 mg, 12%). 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)
  4. custompurified by silica-gel chromatography

Sources & evidence

ORD record
ord-eeaee31cb24d4f38ae82735a1b789e51
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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