n-[3-(4-Fluorophenyl)-propyl]-o-methyl-hydroxylamine → 2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-[3-(4-fluorophenyl)-propyl]-n-methoxy-acetamide

HRID 2181142Notes

Reaction equation

HRID 2181142 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8](Cl)=[O:9])[C:4](=[O:11])[O:3]1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][NH:23][O:24][CH3:25])=[CH:16][CH:15]=1>>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:23]([CH2:22][CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=2)[O:24][CH3:25])=[O:9])[C:4](=[O:11])[O:3]1

Participants

3

Reactant 2

HCID 22485663n-[3-(4-Fluorophenyl)-propyl]-o-methyl-hydroxylamineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 738555872-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-[3-(4-fluorophenyl)-propyl]-n-methoxy-acetamideYield 97%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with N-[3-(4-fluorophenyl)-propyl]-O-methyl-hydroxylamine as described in the preparation of compound 1-C gave the title amide as white crystals (97% yield): mp 90-91° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.77 (6H, s, CH3), 1.98 (2H, m, CH2), 2.64 (2H, t, J=7.9 Hz, CH2), 3.71 (2H, t, J=7.6 Hz, NCH2), 3.73 (3H, s, OCH3), 6.41 (1H, broad s, CH), 6.98 (2H, m, aromatics), 7.16 (2H, m, aromatics). Anal. calcd for C17H20FNO5: C, 60.53; H, 5.98; N, 4.15. Found: C, 60.43; H, 5.99; N, 4.09.

Sources & evidence

ORD record
ord-d525e34a5c024403a9e7be75361be4db
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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