Hydrogen Bromide → HCID 71093699, compound

HRID 57560Notes

Reaction equation

HRID 57560 reaction equation
[CH3:1][CH:2]1[CH2:7][N:6]([C:8]2[CH:14]=[CH:13][C:11](N)=[CH:10][CH:9]=2)[CH2:5][CH2:4][O:3]1.N([O-])=O.[Na+].[OH-].[Na+].[BrH:21]>O>[Br:21][C:11]1[CH:13]=[CH:14][C:8]([N:6]2[CH2:5][CH2:4][O:3][CH:2]([CH3:1])[CH2:7]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 167751034-(2-Methylmorpholin-4-YL)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 71093699HCID 71093699, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(2-methylmorpholino)aniline (7.21 g, 37.5 mmol) in 100 mL HBr in water (40%), a solution of NaNO2 (2.59 g, 37.5 mmol) in 15 mL water was added slowly at −10° C.˜0° C. The mixture was stirred for 30 minutes and was added dropwise to a solution of CuBr (2.96 g, 20.6 mmol) in 30 mL HBr in water (40%). The resulting mixture was stirred and heated at 60° C. for 2 hours. Then the reaction solution was adjusted by 2N NaOH solution to pH>7. Extracted by EA, the combined organic phase was washed with brine, dried and concentrated to give crude product as black oil. MS (m/z): 256 (M+H)+; 258 (M+3)+.

Workup

  1. stirringThe resulting mixture was stirred
  2. extractionExtracted by EA
  3. washthe combined organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give crude product as black oil

Sources & evidence

ORD record
ord-dff15d87ec684bfcbce996bf4078e85c
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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