4-Ethylaniline → 8-(3,3-Dimethyl-butyryl)-2-(4-ethyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194017Notes

Reaction equation

HRID 2194017 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][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8][CH2:7]1)=[O:5])C.[Cl-].C[Al+]C.[CH2:27]([C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)[CH3:28]>CCCCCCC>[CH3:17][C:14]([CH3:15])([CH3:16])[CH2:13][C:12]([N:9]1[CH2:8][CH2:7][C:6]2([C:4](=[O:5])[N:33]([C:32]3[CH:34]=[CH:35][C:29]([CH2:27][CH3:28])=[CH:30][CH:31]=3)[CH2:20][CH2:19]2)[CH2:11][CH2:10]1)=[O:18]

Participants

5

Reactant 3

HCID 115044-EthylanilineHCID 16686359Dimethylalumanylium chlorideHCID 667874921-(3,3-Dimethyl-butyryl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 498022478-(3,3-Dimethyl-butyryl)-2-(4-ethyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 69.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) 1-(3,3-Dimethyl-butyryl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.15 g), dimethylaluminium chloride in heptane (1.0 molar, 0.96 ml) and 4-ethylaniline (0.087 g) to give the desired 8-(3,3-dimethyl-butyryl)-2-(4-ethyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (0.118 g) as an off-white solid. MS (ESI): 357.25 (MH+).

Sources & evidence

ORD record
ord-1315ab29b49d40a19e68fd8877f44673
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

Loading…