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US 9,957,283 B1Granted
Processes for making alkylated arylpiperazine and alkylated arylpiperidine compounds including novel intermediates
AssigneeJohnson Matthey Public Limited Company
InventorsDaniel J. Coughlin, Jeremy C. Wilt, Da-Ming Gou, Steven Collier
Life of this patent
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Abstract
Novel processes, and intermediates, for making alkylated arylpiperazine and alkylated arylpiperidine compounds of the general formulas (I) and (VII), respectively wherein, R1 and R2 are individually selected from hydrogen, alkyl, substituted or alkyl; n=0, 1, or 2; Y=NR3R4, OR5, or SR5, where R3 and R4 are individually selected from acyl or sulfonyl, and where R5 is aryl or heteroaryl, or heterocyclic; and Ar is an aryl, heteroaryl, or heterocyclic compound.
Claims6
A method of preparing
- wherein
- Y is selected from the group consisting of
- and
- Ar is selected from the group consisting of
- provided that when Y is
- then Ar is
- or when Y is
- then Ar is
- or when Y is
- then Ar is
- comprising
- (i) alkylating 1,3,2-dioxathiane 2,2-dioxide having the formula
- with
- in the presence of base selected from potassium carbonate, sodium carbonate, magnesium carbonate, calcium carbonate, potassium hydroxide, sodium hydroxide, magnesium hydroxide or calcium hydroxide, to form the corresponding alkylation compound of the formula
- wherein Q is potassium, sodium, magnesium or calcium,
- (ii) hydrolyzing the alkylation compound of step (i) with aqueous acid to obtain the corresponding hydroxyl compound of formula
- wherein Y is selected from the group consisting of
- (iii) converting the compound of formula
- of step (ii) to the corresponding alkylating agent compound of formula
- wherein LG is an aryl sulfonate or alkyl sulfonate, and
- (iv) alkylating the compound of formula
- of step (iii) with the compound of formula
- wherein Ar is selected from the group consisting of
- in the presence of base selected from potassium carbonate, sodium carbonate, magnesium carbonate, calcium carbonate, potassium hydroxide, sodium hydroxide, magnesium hydroxide or calcium hydroxide,
- provided that when Y is
- then Ar is
- or when Y is
- then Ar is
- or when Y is
- then Ar is
27 more elements
Dependencies are inferred from the claim text.