Morpholine → (4-Bromo-2-nitro-phenyl)-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-amine

HRID 1716379Notes

Reaction equation

HRID 1716379 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:23])([CH3:22])[CH2:10]OS(C2C=CC(C)=CC=2)(=O)=O)=[C:4]([N+:24]([O-:26])=[O:25])[CH:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:23])([CH3:22])[CH2:10][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[C:4]([N+:24]([O-:26])=[O:25])[CH:3]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 58811481HCID 58811481, compound

Product 1

HCID 58811480(4-Bromo-2-nitro-phenyl)-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-amine

Conditions

Temperature
105 °C

Procedure

In a 250 mL flask, mix toluene-4-sulfonic acid 2-(4-bromo-2-nitro-phenylamino)-2-methyl-propyl ester (19.5 g, 44 mmol) and morpholine (50 mL). Heat at 100-110° C. for 2 days. Follow the progress of the reaction by HPLC. Cool the reaction and partition between water and EtOAc. Wash the organic layer with water (2×), dry (MgSO4) and concentrate to give 14 g dark oil. Recrystallize from heptane (400 mL) to give 11 g that is 80% pure by HPLC. Recrystallize a second time to give 6.6 g (42%) orange crystals; MS (es) 358, 360 (M+1), HPLC (ISO80-10M) t=3.17 (94%).

Workup

  1. customthe progress of the reaction by HPLC
  2. temperatureCool
  3. customthe reaction
  4. custompartition between water and EtOAc
  5. washWash the organic layer with water (2×)
  6. dry with materialdry (MgSO4)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-d2cd2e4d56984502a8d7628355416adc
Source dataset
uspto-grants-2010_09
Patent number
US07803814B2

Reaction notes

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