Iodoethane → N-[4-(cyclopropylmethoxy)phenylmethyl]-N-ethoxy-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]-piperidinium iodide

HRID 482281Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N+:13]3([O-:41])[CH2:18][CH2:17][CH:16]([C:19]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=4)([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=4)[OH:20])[CH2:15][CH2:14]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[CH2:42]([I:44])[CH3:43]>C(#N)C>[I-:44].[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N+:13]3([O:41][CH2:42][CH3:43])[CH2:14][CH2:15][CH:16]([C:19]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:38])([F:39])[F:40])=[CH:33][CH:32]=4)([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=4)[OH:20])[CH2:17][CH2:18]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred mixture of 1.0 gram (0.002 mole) of N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxy-methyl]piperidine N-oxide, 0.3 gram (0.002 mole) of ethyl iodide, and about 5.0 mL of acetonitrile was heated at reflux for several hours. The reaction mixture was then cooled to 0° C., and petroleum ether was added. Upon completion of the addition the mixture was filtered and the filtrate was concentrated under reduced pressure, yielding 0.6 gram of N-[4-(cyclopropylmethoxy)phenylmethyl]-N-ethoxy-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]-piperidinium iodide. The NMR spectrum was consistent with the proposed structure.

Workup

temperaturewas heated
temperatureat reflux for several hours
additionUpon completion of the addition the mixture
filtrationwas filtered
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-1189176dbe0e4db39aa581e346137e26
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05795901

Reaction notes

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