Methyl iodide → 1-(4-chlorobenzyl)-1-methyl-4-[[N-[3-(trifluoromethyl)benzoyl]glycyl]aminomethyl]piperidinium iodide

HRID 133627Notes

Reaction equation

HRID 133627 reaction equation
[CH3:1][I:2].[Cl:3][C:4]1[CH:34]=[CH:33][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1>C(#N)C>[I-:2].[Cl:3][C:4]1[CH:34]=[CH:33][C:7]([CH2:8][N+:9]2([CH3:1])[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:30])[F:28])[CH:22]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 508750N-({[1-(4-Chloro-benzyl)-piperidin-4-ylmethyl]-carbamoyl}-methyl)-3-trifluoromethyl-benzamide

Product 1

HCID 184262121-(4-chlorobenzyl)-1-methyl-4-[[N-[3-(trifluoromethyl)benzoyl]glycyl]aminomethyl]piperidinium iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Methyl iodide (28 mg, 0.20 mmol) was added to an acetonitrile (2.0 mL) solution of 1-(4-chlorobenzyl)-4-[[N-[3-(trifluoromethyl)benzoyl]glycyl]aminomethyl]piperidine. The resulting reaction mixture was stirred at 70° C. for 4 hours. The solvent was removed under reduced pressure to provide 1-(4-chlorobenzyl)-1-methyl-4-[[N-[3-(trifluoromethyl)benzoyl]glycyl]aminomethyl]piperidinium iodide as yellow oil. (31.7 mg, 71%). The purity was determined by RPLC/MS (99%). ESI/MS m/e 482.1 (M++H, C24H28ClF3N3O2).

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cd93ec5c6fd54ae0bc28cc566ce72537
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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