Anisole → [1,4]Bipiperidinyl-2-thione

HRID 2221077Notes

Reaction equation

HRID 2221077 reaction equation
C1(OC)C=CC=CC=1.C(OC([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]2=[S:31])[CH2:21][CH2:20]1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.CO>[N:25]1([CH:22]2[CH2:23][CH2:24][NH:19][CH2:20][CH2:21]2)[CH2:30][CH2:29][CH2:28][CH2:27][C:26]1=[S:31]

Participants

7

Reactant 4

HCID 7519AnisoleHCID 11430Potassium CarbonateHCID 24436Sodium SulfateHCID 233699572-Thioxo-[1,4']bipiperidinyl-1'-carboxylic acid benzyl ester

Product 1

HCID 23369948[1,4]Bipiperidinyl-2-thione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Anisole (2.5 mL) was added to a solution of 2-thioxo-[1,4′]bipiperidinyl-1′-carboxylic acid benzyl ester (2.4 g) in methylene chloride (40 mL) at 0° C. followed by the addition of trifluorosulfonic acid (3.4 mL). After 30 minutes, solid potassium carbonate was added, then sodium sulfate and methanol. The solids were removed by filtration and the filtrate was concentrated. The residue was dissolved in methanol and neutralized by passage through a column of Amberlyst A-21 (slightly basic) resin. The filtrate was collected and concentrated and purified by chromatography, with methylene chloride:methanol (gradient 95:5, 90:10) as eluent. The title compound was obtained as a white solid (0.93 g). MS: m/z=199 (M+H).

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in methanol
  4. customThe filtrate was collected
  5. concentrationconcentrated
  6. custompurified by chromatography, with methylene chloride

Sources & evidence

ORD record
ord-f64ab98eb11f4ff7823caedd4b5c605b
Source dataset
uspto-grants-2008_05
Patent number
US07368461B2

Reaction notes

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