1-Iodopropane → N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-N-propyl-acetamide

HRID 2211916Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([CH3:14])[CH:5]=1.I[CH2:16][CH2:17][CH3:18]>>[Cl:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:16][CH2:17][CH3:18])[C:11](=[O:13])[CH3:12])=[C:6]([CH3:14])[CH:5]=1

Participants

Reactant 2

HCID 336431-Iodopropane

HCID 21963464N-[4-(2-Chloro-ethyl)-2-methyl-phenyl]-acetamide

Product 1

HCID 21963280N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-N-propyl-acetamideYield 90%

Procedure

N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-N-propyl-acetamide was prepared according to the general method as outlined in Preparation 43 starting from N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-acetamide (0.400 g, 1.89 mmol) and iodopropane (0.230 mL, 2.36 mmol). After chromatographic purification, the product was isolated as a viscous oil (0.432 g, 1.701 mmol). Yield=90%. MS (APCI): 254 [M+H]+; 1H NMR (400 MHz, CDCl3D2O) δ 7.13 (bs, 1H), 7.07 (bd, J=7.77 Hz, 1H), 7.00 (d, J=7.77 Hz, 1H), 4.8 (bs, H2O/D20), 4.03–3.91 (m, 1H), 3.71 (t, J=8.12 Hz, 2H), 3.11–2.99 (m, 3H), 2.20 (s, 3H), 1.72 (s, 3H), 1.64–1.41 (m, 2H), 0.87 (t, J=6.34 Hz, 3H).

Workup

customAfter chromatographic purification

Sources & evidence

ORD record: ord-f831b7fb23614b8b909a41a0e9fe8169
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101886B2

Reaction notes

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