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

HRID 482281
Notes
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Reaction equation

HRID 482281 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 53988844HCID 53988844, compound

Product 1

HCID 19063887N-[4-(cyclopropylmethoxy)phenylmethyl]-N-ethoxy-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]-piperidinium iodideYield 40.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. temperaturewas heated
  2. temperatureat reflux for several hours
  3. additionUpon completion of the addition the mixture
  4. filtrationwas filtered
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes