4-(Trifluoromethoxy)aniline → 2-(4-(Trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one

HRID 2194229Notes

Reaction equation

HRID 2194229 reaction equation
C(O[C:4]([C:6]1([CH2:19][CH2:20]OC)[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[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:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1>CCCCCC>[F:27][C:28]([F:37])([F:38])[O:29][C:30]1[CH:31]=[CH:32][C:33]([N:36]2[CH2:20][CH2:19][C:6]3([CH2:7][CH2:8][NH:9][CH2:10][CH2:11]3)[C:4]2=[O:5])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 582872614-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 667427592-(4-(Trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) from 4-(2-methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester, dimethylaluminium chloride in hexane and 4-trifluoromethoxy-phenylamine, with concomitant cleavage of the Boc protecting group at the reaction conditions applied. MS (ESI): 315.2 (MH+).

Sources & evidence

ORD record
ord-d86a8b5a938c4dc6986b255d4b1d64ac
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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