4-(Trifluoromethoxy)aniline → 8-(3-Cyclopropyl-propionyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194008Notes

Reaction equation

HRID 2194008 reaction equation
C(O[C:4]([C:6]1([CH2:19][CH2:20]OC)[CH2:11][CH2:10][N:9]([C:12](=[O:18])[CH2:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:8][CH2:7]1)=[O:5])C.[Cl-].C[Al+]C.[F:27][C:28]([F:38])([F:37])[O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1>CCCCCCC>[CH:15]1([CH2:14][CH2:13][C:12]([N:9]2[CH2:8][CH2:7][C:6]3([C:4](=[O:5])[N:34]([C:33]4[CH:35]=[CH:36][C:30]([O:29][C:28]([F:27])([F:37])[F:38])=[CH:31][CH:32]=4)[CH2:20][CH2:19]3)[CH2:11][CH2:10]2)=[O:18])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 667870191-(3-Cyclopropyl-propionyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 498019598-(3-Cyclopropyl-propionyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 15.9%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) from 1-(3-cyclopropyl-propionyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.1 g), dimethylaluminium chloride in heptane (0.9 molar, 0.71 ml) and 4-trifluoromethoxyanilin (0.057 g) to give the desired 8-(3-cyclopropyl-propionyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (0.021 g) as an off-white solid. MS (ESI): 449.17 (MH+).

Sources & evidence

ORD record
ord-9cf873750252486983dbbf4a4a98f32a
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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