Morpholine → 5,5-Dichloro-1-morpholinopent-4-ene-1,3-dione

Temperature

15 °C

Two separate solutions of 1 (62.5 g, 0.26 mmol) and morpholine (24.0 g, 0.28 mol) in DCM (120 ml) were added simultaneously to a mixture of NaHCO3 (44.0 g, 0.52 mol) in dry DCM (300 ml). The reaction was maintained at 15° C. over 140 minutes with stirring. The reaction was filtered, washed with DCM (3×100 ml) and the combined organic layers were concentrated in vacuo to a slurry which was then passed through a short silica pad, and further washed with DCM (4×100 ml). The combined organic layers were concentrated in vacuo, suspended in hexane (400 ml) and stirred for 1 hour, filtered and dried to give a cream solid. The solid was suspended in TBME (100 ml), stirred for 15 minutes, filtered, washed with TBME and dried to give 2 as a white powder (47.8 g, 72%). m/z (LC-MS, ESP): 252 (M++1).

1. filtrationThe reaction was filtered
2. washwashed with DCM (3×100 ml)
3. concentrationthe combined organic layers were concentrated in vacuo to a slurry which
4. washfurther washed with DCM (4×100 ml)
5. concentrationThe combined organic layers were concentrated in vacuo
6. stirringstirred for 1 hour
7. filtrationfiltered
8. customdried
9. customto give a cream solid
10. stirringstirred for 15 minutes
11. filtrationfiltered
12. washwashed with TBME
13. customdried

ORD record

ord-cb8da939f9bf4f809d14100d2c468f8c

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07429660B2