tert-Butyl 2-[({[(4-chlorophenyl)amino]carbonyl}amino)methyl]morpholine-4-carboxylate → N-(4-Chlorophenyl)-N'-(morpholin-2-ylmethyl)urea

HRID 1371383Notes

Reaction equation

HRID 1371383 reaction equation
[Cl:1][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(OC(C)(C)C)=O)[CH2:14]2)=[O:10])=[CH:4][CH:3]=1>Cl.O1CCOCC1>[Cl:1][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][NH:15][CH2:14]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 21070807tert-Butyl 2-[({[(4-chlorophenyl)amino]carbonyl}amino)methyl]morpholine-4-carboxylate

Product 1

HCID 23089254N-(4-Chlorophenyl)-N'-(morpholin-2-ylmethyl)ureaYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Intermediate 8 (1.9 g) was stirred in 4.0M hydrogen chloride in 1,4-dioxane (40 ml) at 22° C. for 30 min. The solvent was removed in vacuo and the residue was purified by solid phase extraction (Isolute SCX sulphonic acid column), eluting with methanol followed by 10% 0.880 NH3 solution in methanol, to give the title compound as a cream foam (1.15 g). LC/MS (System A) Rt 2.03 min, Mass Spectrum m/z 270 [MH+].

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by solid phase extraction (Isolute SCX sulphonic acid column)
  3. washeluting with methanol

Sources & evidence

ORD record
ord-dd7ec61839e54caf946eb333ab3e4952
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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