Benzyl 2-[({[(4-chlorophenyl)amino]carbonyl}amino)methyl]morpholine-4-carboxylate → N-(Morpholin-2-ylmethyl)-N'-phenylurea

HRID 1371381Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][N:15](C(OCC3C=CC=CC=3)=O)[CH2:14]2)=[O:10])=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[NH:15]1[CH2:16][CH2:17][O:18][CH:13]([CH2:12][NH:11][C:9]([NH:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[O:10])[CH2:14]1

Participants

Conditions

Temperature: 22 °C

Procedure

A suspension of 10% palladium on carbon (1.5 g) and Intermediate 6 (3.2 g) in ethyl acetate (250 ml) was stirred vigorously under hydrogen at 1 atmosphere and 22° C. for 20 h. The catalyst was filtered off and the volatiles were removed in vacuo. The procedure was repeated with a further portion of the catalyst (1 g) for a further 24 h before filtration and solvent evaporation in vacuo. Purification of the residue by Biotage flash chromatography on a 90 g silica cartridge, eluting with 100:8:1 dichloromethane/ethanol/0.880 ammonia solution, gave the title compound as a colourless oil (1.6 g). LC/MS (System A) Rt 1.39 min, Mass Spectrum m/z 236 [MH+].

Workup

filtrationThe catalyst was filtered off
customthe volatiles were removed in vacuo
filtrationThe procedure was repeated with a further portion of the catalyst (1 g) for a further 24 h before filtration and solvent evaporation in vacuo
customPurification of the residue by Biotage flash chromatography on a 90 g silica cartridge
washeluting with 100:8:1 dichloromethane/ethanol/0.880 ammonia solution

Sources & evidence

ORD record: ord-f07dfc3c9a7a48f59ba8587fbc63a7a5
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157457B2

Reaction notes

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