Water → 4-(4-Bromophenyl)morpholine

HRID 2179573Notes

Reaction equation

HRID 2179573 reaction equation
[Br:1]Br.[C:3]1([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:6]1[CH:7]=[CH:8][C:3]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 623394-Phenylmorpholine

Product 1

HCID 116228514-(4-Bromophenyl)morpholine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 6.94 ml (134.8 mmol) of bromine in 25 ml of acetic acid is slowly added dropwise over a period of 40 min to a solution of 20 g (122.5 mmol) of N-phenylmorpholine in 170 ml of acetic acid at room temperature. After stirring at room temperature for 30 min, the reaction mixture is stirred into 750 ml of water and adjusted to pH 11 with 45% strength sodium hydroxide solution. The resulting precipitate is filtered off with suction, washed with water and dried under high vacuum. Recrystallization from ethanol results in 18.6 g (62.9% of theory) of the title compound.

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. washwashed with water
  3. customdried under high vacuum
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-201cbd3f4f794a7e997eac62299d91d8
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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