4-Isopropoxyaniline → 8-Benzenesulfonyl-2-(4-isopropoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2193998Notes

Reaction equation

HRID 2193998 reaction equation
C([O:3][C:4]([C:6]1([CH2:21][CH2:22]OC)[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[Cl-].C[Al+]C.[CH:29]([O:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1)([CH3:31])[CH3:30]>CCCCCCC>[C:15]1([S:12]([N:9]2[CH2:8][CH2:7][C:6]3([C:4](=[O:3])[N:37]([C:36]4[CH:38]=[CH:39][C:33]([O:32][CH:29]([CH3:31])[CH3:30])=[CH:34][CH:35]=4)[CH2:22][CH2:21]3)[CH2:11][CH2:10]2)(=[O:13])=[O:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 821124-IsopropoxyanilineHCID 16686359Dimethylalumanylium chlorideHCID 667870971-Benzenesulfonyl-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 498016518-Benzenesulfonyl-2-(4-isopropoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 58.1%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) from 1-benzenesulfonyl-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.2 g), dimethylaluminium chloride in heptane (0.9 molar, 0.94 ml) and 4-isopropoxy-aniline (0.1 g) to give the desired 8-benzenesulfonyl-2-(4-isopropoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (0.14 g) as a yellow solid. MS (ESI): 429.18 (MH+).

Sources & evidence

ORD record
ord-0b0518b1a83047769eeefa84fe12f0c6
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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