Fluorinating reactants and process for their preparation

摘要

alpha,alpha-Difluoroalkylamines (I) are new. Also new are mixtures (A) containing (a) a broader class of alpha,alpha-difluoroalkylamines (I'), (b) an aprotic tertiary amine having no fluoro atoms in the alpha-position relative to nitrogen and/or a N-heteroaromatic compound and (c) hydrogen fluoride; and some specific dichloro compound intermediates. alpha,alpha-Difluoroalkylamines of formula R1-CF2-NR2R3 (I) are new. R1 = H, 1-12C alkyl, ((2-12C) alkylene-O)n-(1-12C) alkyl, 4-15C aralkyl or 3-14C heteroaryl; n = 1-5; R2, R3 = 4-15C aralkyl or 1-12C alkyl; or R2 + R3 or R1 + R2 and/or R3 = group completing a 3-12C cyclic group; the compounds 1,1-difluoromethyl-N,N-dimethylamine, 1,1-difluoromethyl-N,N-diethylamine, 1,1-difluoromethyl-N,N-diisopropylamine and 1,1-difluoro-N,N-2-trimethyl-1-propanamine are excluded. Independent claims are included for: (a) new mixtures (A) comprising (a) alpha,alpha-difluoroalkylamines of formula R4-CF2-NR5R6 (I'), (b) at least one aprotic tertiary amine having no fluoro atoms in the alpha-position relative to the nitrogen and/or at least one N-heteroaromatic compound and (c) hydrogen fluoride; (b) the preparation of (I) and (A); and (c) the following new geminal dichloro compound intermediates: 1,1-dichloromethyl-N,N-dimethylamine, 1,1-dichloromethyl-N,N-diethylamine, 1,1-dichloromethyl-N,N-diisopropylamine, 1,1-dichloro-N,N-2-trimethyl-1-propanamine, 1,1-dichloro-N,N-2,2-tetramethyl-1-propanamine (VIa), N,N-diethyl-alpha,alpha-dichloro-2,2-dimethyl-1-propanamine, N-(1,1-dichloromethyl)-morpholine, 1,1-dichloro-N,N-dimethyl-phenylmethanamine, N,N-diethyl-alpha,alpha-dichloro-3-pyridyl-methanamine and 2,2-dichloro-1,3,3-trimethylpyrrolidine. R4 = H, 1-12C alkyl, ((2-12C) alkylene-O)n-(1-12C) alkyl, 3-14C aryl or NR7R8; n = 1-5; R7, R8 = 1-8C alkyl; or NR7R8 = 4-7 membered cyclic residue with a total of 3-12C; R5, R6 = 1-12C alkyl; or R5 + R6 or R4 + R5 and/or R6 = group completing a 4-12C cyclic group.