Triethylamine → 4-morpholino-N-(4-nitrophenoxycarbonyl)aniline

HRID 993158Notes

Reaction equation

HRID 993158 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:23]>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:22]([O:24][C:25]3[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=3)=[O:23])=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 821294-Nitrophenyl chloroformate

Product 1

HCID 227075274-morpholino-N-(4-nitrophenoxycarbonyl)aniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.60 g (14.6 mmol) of 4-morpholinoaniline in 20 ml of methylene chloride were added 14.07 ml (105 mmol) of triethylamine and 3.53 g (17.5 mmol) of 4-nitrophenyl chloroformate under ice-cooling, followed by stirring at room temperature for 7 hours. After the solvent was evaporated, water was added to the residue, and the precipitated crystals were collected by filtration, washed water, and dried to give 4-morpholino-N-(4-nitrophenoxycarbonyl)aniline.

Workup

  1. temperaturecooling
  2. customAfter the solvent was evaporated
  3. additionwater was added to the residue
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed water
  6. customdried

Sources & evidence

ORD record
ord-55a333a62bdf47e6b48949ffe7d94199
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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