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

HRID 30279Notes

Reaction equation

HRID 30279 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=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:18]3[CH:17]=[CH:16][S:15][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 862291041-Benzyl-4-thiophen-2-yl-piperidine-3-carbonyl chloride

Product 1

HCID 597894266-Benzyl-3b,4,5,6,7,7a-hexahydro-3-thia-6-aza-cyclopenta[alpha]inden-8-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from step d) (7.37 g, 20.7) mmol) in CH2Cl2 (103 ml) was added dropwise to a slurry of AlCl3 (8.26 g, 62 mmol) in CH2Cl2 (28 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 4 g (68%) of the subtitle compound. 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-9728e2b86ef14aee8d8c55b6fea98cd6
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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