4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Base Information

Chemical Name:4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester
CAS No.:305794-58-5
Molecular Formula:C₂₄H₃₆N₂O₃S
Molecular Weight:432.627
Hs Code.:

4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid <i>tert</i>-butyl ester

Synonyms:4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

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Chemical Property of 4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

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Technology Process of 4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

There total 8 articles about 4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

: 305794-45-0
4-(4-bromobenzoyl)-1'-(tert-butoxycarbonyl)-4'-methyl-1,4'-bipiperidine

: 5188-07-8
sodium thiomethoxide

: 305794-58-5
4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Guidance literature:: In N,N-dimethyl-formamide; at 70 ℃; for 12h;

Reference yield:

: 498-94-2
isonipecotic acid

: 305794-58-5
4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 4 h / Heating

2: SOCl₂ / Heating

3: AlCl₃ / 4 h / Heating

4: p-TsOH / Heating

5: 95 percent / aq. K₂CO₃ / methanol / 20 °C

6: Ti(OiPr)4 / 1,2-dichloro-ethane / 12 h / 20 °C

7: 7.3 g / 3 h / 20 °C

8: 98 percent / MeMgBr / tetrahydrofuran; diethyl ether / 2 h / 20 °C

9: 6 N HCl / ethyl acetate / 24 h / 20 °C

10: 5.1 g / 10percent aq. NaOH / 20 °C

11: dimethylformamide / 24 h / 70 °C

With titanium(IV) isopropylate; hydrogenchloride; aluminium trichloride; thionyl chloride; methylmagnesium bromide; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 3: Friedel-Crafts acylation;
DOI:10.1021/jm0200815

Reference yield:

: 126501-71-1
1-(2,2,2-trifluoroacetyl)piperidine-4-carbonyl chloride

: 305794-58-5
4'-methyl-4-(4-methylsulfanyl-benzoyl)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: AlCl₃ / 4 h / Heating

2: p-TsOH / Heating

3: 95 percent / aq. K₂CO₃ / methanol / 20 °C

4: Ti(OiPr)4 / 1,2-dichloro-ethane / 12 h / 20 °C

5: 7.3 g / 3 h / 20 °C

6: 98 percent / MeMgBr / tetrahydrofuran; diethyl ether / 2 h / 20 °C

7: 6 N HCl / ethyl acetate / 24 h / 20 °C

8: 5.1 g / 10percent aq. NaOH / 20 °C

9: dimethylformamide / 24 h / 70 °C

With titanium(IV) isopropylate; hydrogenchloride; aluminium trichloride; methylmagnesium bromide; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Friedel-Crafts acylation;
DOI:10.1021/jm0200815