N-bromobutanimide → 2-Bromo-4-(2-morpholin-4-yl-ethyl)-phenylamine

HRID 1508092Notes

Reaction equation

HRID 1508092 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-])=O.C1C(=O)N([Br:25])C(=O)C1>CO.C(Cl)Cl.[Pd]>[Br:25][C:5]1[CH:6]=[C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 27974734-[2-(4-Nitrophenyl)ethyl]morpholine

Product 1

HCID 589944272-Bromo-4-(2-morpholin-4-yl-ethyl)-phenylamineYield 58%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution 4-[2-(4-nitro-phenyl)-ethyl]-morpholine (0.70 g, 2.97 mmol) (as prepared in the previous step) in 15 mL of MeOH was added 10% Pd/C (30 mg) and the mixture hydrogenated under 20 psi of H2 for 2 h. The mixture was filtered though Celite and concentrated. The residue was dissolved in DCM (20 mL) and NBS (0.53 g, 2.97 mmol) was added and the reaction stirred for 20 min at RT. The reaction was diluted with DCM (20 mL) and washed with NaHCO3 (2×40 mL) and the organic layer dried over Na2SO4 and concentrated. The title compound was eluted from a 20-g SPE with 100% EtOAc to give 0.49 g (58%) of a light yellow oil. Mass spectrum (ESI, m/z): Calcd. for C12H17BrN2O, 285.0 (M+H). found 285.0.

Workup

  1. filtrationThe mixture was filtered though Celite
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM (20 mL)
  4. washwashed with NaHCO3 (2×40 mL)
  5. dry with materialthe organic layer dried over Na2SO4
  6. concentrationconcentrated
  7. washThe title compound was eluted from a 20-g SPE with 100% EtOAc

Sources & evidence

ORD record
ord-b31ea82dad0d4dab8f5062a08d7d45bc
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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