4-Fluoro-2-(trifluoromethyl)benzenesulfonyl Chloride → 8-(4-Fluoro-2-trifluoromethyl-benzenesulfonyl)-2-[4-(2,2,2-trifluoro-ethyl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194068Notes

Reaction equation

HRID 2194068 reaction equation
C(O[C:4]([C:6]1([CH2:12][CH2:13]OC)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])C.[F:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1.[F:31][C:32]([F:42])([F:41])[CH2:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:9]2[CH2:8][CH2:7][C:6]3([C:4](=[O:5])[N:38]([C:37]4[CH:39]=[CH:40][C:34]([CH2:33][C:32]([F:31])([F:41])[F:42])=[CH:35][CH:36]=4)[CH2:13][CH2:12]3)[CH2:11][CH2:10]2)(=[O:25])=[O:24])=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1

Participants

4

Reactant 3

HCID 27375484-Fluoro-2-(trifluoromethyl)benzenesulfonyl ChlorideHCID 148368584-(2,2,2-Trifluoroethyl)anilineHCID 567539694-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 498005008-(4-Fluoro-2-trifluoromethyl-benzenesulfonyl)-2-[4-(2,2,2-trifluoro-ethyl)-phenyl]-2,8-diaza-spiro[4.5]decan-1-one

Procedure

Off-white solid. MS (ESI): 539.12 (MH+). This example was prepared in analogy to example 1 step C) to D) from 4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (example 1 step B)), 4-fluoro-2-trifluoromethyl-benzenesulfonyl chloride and 4-(2,2,2-trifluoroethyl)-aniline.

Sources & evidence

ORD record
ord-0f822e37277f4ad3a8f753e648434412
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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