α, α-dibromo-α-chloro-acetophenones as synthons
AssigneeGeneva Pharmaceuticals, Inc.
InventorsAnup K. Ray, Hiren Patel, Shilpa V. Merai, Mahendra R. Patel
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Abstract
This disclosure relates to the use of α,α-dibromo-α-chloroacetophenone compounds as intermediates for the preparation of aromatic carbonyl compounds, especially aromatic amides. The compound 2,5-bis(2,2,2-trifluoroethoxy)-α,α-dibromo-α-chloroacetophenone is especially useful as an intermediate for the preparation of flecainide, a known pharmaceutical.
Claims15
A process for the preparation of 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide or a salt thereof, which comprises:
- (a) reacting 2,5-bis(2,2,2-trifluoroethoxy)-α,α-dibromo-α-chloro acetophenone with 2-(aminomethyl)pyridine to form 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)-benzamide, and
- (b) reducing the 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)-benzamide.
2,5-bis(2,2,2-trifluoroethoxy)-α,α-dibromo-α-chloro-acetophenone.
A process for the preparation of 2,5-bis(2,2,2-trifluoroethoxy)-α,α-dibromo-α-chloro acetophenone which comprises reacting 2,5-bis(2,2,2-trifluoroethoxy)-α-chloro acetophenone with bromine.
A process for the preparation of 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)-benzamide which comprises reacting 2,5-bis(2,2,2-trifluoroethoxy)-α,α-dibromo-α-chloro acetophenone with 2-(aminomethyl)pyridine.
A compound of the formula
- wherein R1 and R2 are independently hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C1-C6-alkoxy, —N(C1-C6-alkyl)2, —S—C1-C6-alkyl, or phenyl, wherein the alkyl groups are unsubstituted or substituted by one or more halogen, hydroxy, —S—alkyl, —O—alkyl, carboxy, amido, or ester groups and when the R1 or R2 substituent is phenyl it is unsubstituted or substituted in the phenyl ring by halogen, C1-C6-alkyl, C3-C7-cycloalkyl, C1-C6-alkoxy, —N(C1-C6-alkyl)2, —S—C1-C6-alkyl, the alkyl groups of which are unsubstituted or substituted by one or more halogen, hydroxy, —S—alkyl, —O—alkyl, carboxy, amido, or ester groups;
- or R1 and R2 together with the phenyl ring carbons to which they are attached form a 5-7 member aliphatic, aromatic, heterocyclic, or heteroaromatic ring.
Dependencies are inferred from the claim text.