Methyl iodide → 4-(2-Ethoxy-2-oxoethyl)-1,1-dimethyl-4-(3-(4-octylphenyl)ureido)piperidinium iodide

HRID 1192887Notes

Reaction equation

HRID 1192887 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=2)=[O:10])[CH2:4][CH2:3]1.[CH3:32][I:33]>C(Cl)Cl>[I-:33].[CH2:30]([O:29][C:27](=[O:28])[CH2:26][C:5]1([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=2)=[O:10])[CH2:6][CH2:7][N+:2]([CH3:32])([CH3:1])[CH2:3][CH2:4]1)[CH3:31]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 66865126Ethyl 2-(1-methyl-4-(3-(4-octylphenyl)ureido)piperidin-4-yl)acetate

Product 1

HCID 668652964-(2-Ethoxy-2-oxoethyl)-1,1-dimethyl-4-(3-(4-octylphenyl)ureido)piperidinium iodideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-(1-methyl-4-(3-(4-octylphenyl)ureido)piperidin-4-yl)acetate (73 mg, 0.169 mmol) in CH2Cl2 (5 mL) was treated with MeI (0.11 mL, 1.69 mmol) and the reaction stirred overnight at room temperature. The solvent was removed in vacuo to yield crude title compound (95 mg, 98%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 8.35 (bs, 1H), 7.42 (d, 2H, J=8.4 Hz), 7.05 (d, 2H, J=8.4 Hz), 6.49 (bs, 1H), 4.39-4.32 (m, 2H), 4.14 (q, 2H, J=7.2 Hz), 3.41-3.34 (m, 5H), 3.21 (s, 2H), 3.20 (s, 3H), 2.64-2.41 (m, 6H), 1.29-1.20 (m, 13H), 0.89 (t, 3H, 6.4 Hz); MS ESI 446.4 [M]+, calcd for [C26H44N3O3]+ 446.65.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4994e647745f44b6a610b78afda9e35f
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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