Hydrogen Bromide → N-[2-(4-Carbomethoxymethoxyphenyl)ethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

HRID 1587935Notes

Reaction equation

HRID 1587935 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH:13]([C:17]3[N:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[S:20][CH:21]=3)[CH2:12]2)=[CH:5][CH:4]=1.Br.C(=O)([O-])[O-].[K+].[K+].BrC[C:35]([O:37][CH3:38])=[O:36]>CC(C)=O>[C:35]([CH2:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH:13]([C:17]3[N:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[S:20][CH:21]=3)[CH2:12]2)=[CH:5][CH:4]=1)([O:37][CH3:38])=[O:36]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 19974138HCID 19974138, compound

Product 1

HCID 19974221N-[2-(4-Carbomethoxymethoxyphenyl)ethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.6 g (1.6 mmol) of N-[2-(4-Methoxyphenyl)ethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine are heated on a steam bath with 6 ml of 48% strength aqueous hydrobromic acid for 3 hours. The mixture is then concentrated, toluene is added, and the mixture is again evaporated to dryness. The foamy residue is boiled under reflux in 15 ml of acetone with 1.2 g (8.7 mmol) of potassium carbonate and 0.3 ml (1.65 mmol) of methyl bromoacetate for 1 hour. The mixture is then filtered, the filtrate is concentrated, and the residue is purified on a silica gel column using toluene/acetone=4:1.

Workup

  1. concentrationThe mixture is then concentrated
  2. additiontoluene is added
  3. customthe mixture is again evaporated to dryness
  4. filtrationThe mixture is then filtered
  5. concentrationthe filtrate is concentrated
  6. customthe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-b5f2cf3f42f04116b505fa58dca08fa3
Source dataset
uspto-grants-1993_06
Patent number
US05219852

Reaction notes

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