Hydrogen Bromide → (S)-3-ethylmorpholine hydrobromide

HRID 72179Notes

Reaction equation

HRID 72179 reaction equation
[CH2:1]([C@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1S(C1C=CC(C)=CC=1)(=O)=O)[CH3:2].C1(O)C=CC=CC=1.[BrH:26]>C(O)(=O)C>[BrH:26].[CH2:1]([C@H:3]1[CH2:8][O:7][CH2:6][CH2:5][NH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 58222512(S)-3-ethyl-4-tosylmorpholine

Product 1

HCID 67094353(S)-3-ethylmorpholine hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(S)-3-ethyl-4-tosylmorpholine (220 mg, 0.82 mmol) and phenol (150 mg, 1.6 mmol) were dissolved in 4.1 M of hydrogen bromide in acetic acid (2.4 mL) and the solution was stirred at room temperature overnight. The reaction was poured on ether and the solid was collected by filtration and washed with ether to give (S)-3-ethylmorpholine hydrobromide (j-1) as a white solid: 1H NMR (400 MHz, CDCl3) δ 3.77-3.60 (m, 3H), 3.60-3.44 (m, 2H), 3.44-3.19 (m, 3H), 1.67 (dtd, J=28.6, 14.0, 7.4 Hz, 2H), 1.31-1.12 (m, 2H), 0.97-0.84 (m, 3H).

Workup

  1. additionThe reaction was poured on ether
  2. filtrationthe solid was collected by filtration
  3. washwashed with ether

Sources & evidence

ORD record
ord-cd062403859348d8919a708e40247b74
Source dataset
uspto-grants-2014_09
Patent number
US08828990B2

Reaction notes

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