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

HRID 1371382Notes

Reaction equation

HRID 1371382 reaction equation
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1.ClCCl.C(O)C.N>ClCCl.CO>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:1][CH2:2][CH:3]2[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]2)=[O:25])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 76934-Chlorophenyl IsocyanateHCID 19081094tert-Butyl 2-(aminomethyl)morpholine-4-carboxylateHCID 21584144Dichloromethane ethanol

Product 1

HCID 21070807tert-Butyl 2-[({[(4-chlorophenyl)amino]carbonyl}amino)methyl]morpholine-4-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-(aminomethyl)morpholine-4-carboxylate (Prepared as described in EP 0 468231, 2.4 g) in dichloromethane (100 ml) was added 4-chlorophenylisocyanate (1.87 g). The mixture was stirred at 22° C. for 16 h before 10% 0.880 ammonia solution in methanol was added. Stirring was continued for a further 30 min before the solvent was removed in vacuo to give the title compound as a white foam (3.98 g).

Workup

  1. additionwas added
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-feabac9a30e146228fb6dc9b13a7417c
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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