N-bromobutanimide → HCID 68450954, compound

HRID 1992004Notes

Reaction equation

HRID 1992004 reaction equation
[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[Br:23][C:11]1[CH:10]=[C:9]([C:6]2[CH2:5][CH2:4][N:3]([O:2][CH3:1])[CH2:8][CH:7]=2)[CH:14]=[CH:13][C:12]=1[NH2:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68439019HCID 68439019, compound

Product 1

HCID 68450954HCID 68450954, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(1-methoxy-piperidin-4-yl)-phenylamine (as prepared above, 42 mg, 0.20 mmol) in DCM (2 mL) was added NBS (36.2 mg, 0.20 mmol) and the reaction mixture was stirred at RT for 12 h. The reaction mixture was diluted with DCM (10 mL) and washed with saturated aqueous NaHCO3 (10 mL) and water (10 mL). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to obtain 2-bromo-4-(1-methoxy-1,2,3,6-tetrahydro-pyridin-4-yl)-phenylamine (43 mg, 74.5%) which was used in the next step without purification.

Workup

  1. washwashed with saturated aqueous NaHCO3 (10 mL) and water (10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2af3244c14749cfaa95f201762050ae
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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