n-(4-Fluorobenzyl)-o-(3-morpholin-4-yl-propyl)-hydroxylamine → 2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(4-fluorobenzyl)-n-(3-morpholin-4-yl-propoxy)-acetamide

HRID 2214728Notes

Reaction equation

HRID 2214728 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:31]=[CH:30][C:17]([CH2:18][NH:19][O:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:16][CH:15]=1>>[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([N:19]([CH2:18][C:17]2[CH:16]=[CH:15][C:14]([F:13])=[CH:31][CH:30]=2)[O:20][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:9])[C:4](=[O:11])[O:3]1

Participants

3

Reactant 2

HCID 21947550n-(4-Fluorobenzyl)-o-(3-morpholin-4-yl-propyl)-hydroxylamineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 738555492-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(4-fluorobenzyl)-n-(3-morpholin-4-yl-propoxy)-acetamideYield 47.4%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride (1.0 mmol) with N-(4-fluorobenzyl)-O-(3-morpholin-4-yl-propyl)-hydroxylamine (0.268 g, mmol) as described in the preparation of compound 44-C (acid wash was skipped in this case) gave 0.200 g (47% yield) of the title amide as a clear oil after chromatography on silica gel. 1HNMR 400 MHz (C6D6) δ (ppm): 1.10 (6H, s, CH3), 1.50 (2H, m, CH2), 2.19 (2H, t, J=6.6 Hz, NCH2), 2.20 (4H, m, NCH2), 3.70 (2H, t, J=6.2 Hz, OCH2), 3.71 (4H, m, OCH2), 4.73 (2H, s, NCH2), 6.85 (3H, m, CH and aromatics), 7.22 (2H, m, aromatics). HRMS (MAB N2) calculated for C21H27FN2O6 [M+]: 422.185315: found: 422.185246.

Workup

  1. washwash

Sources & evidence

ORD record
ord-a4afe710aca74fcf8d7f3b436f99ba8d
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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