Acetone → HCID 21450281, compound

HRID 1579282Notes

Reaction equation

HRID 1579282 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:3]=1.[CH2:15]([Cl:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[ClH:22].[CH2:15]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 21450269HCID 21450269, compound

Product 1

HCID 21450281HCID 21450281, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A well stirred mixture of 4-bromo-2-morpholino phenol (4.44 g, 0.017 mole), benzyl chloride (2.3 ml, 0.02 mole), potassium carbonate (4.75 g, 0.034 mole), and dry acetone (60 ml) was heated under reflux for 7 hours. The mixture was diluted with water, extracted with ether and the combined extracts washed with dilute sodium hydroxide solution and with water. Extraction of the ethereal solution with concentrated hydrochloric acid and evaporation of these extracts under reduced pressure gave 4-benzyloxy-3-morpholinobromobenzene hydrochloride, which was collected and washed with ether (5.29 g, 80%, m.p. 164°-174°C). The hydrochloride, recrystallised from ethanol, had m.p. 168°-177°C. A suspension of the hydrochloride in water was treated with excess potassium carbonate and 4-benzyloxy-3-morpholinobromobenzene extracted into ether. Evaporation of the ether extracts gave the free base, m.p. 84°-87°C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. extractionextracted with ether
  4. washthe combined extracts washed with dilute sodium hydroxide solution and with water
  5. extractionExtraction of the ethereal solution
  6. customwith concentrated hydrochloric acid and evaporation of these extracts under reduced pressure

Sources & evidence

ORD record
ord-db9e58531d1449af976e4fa23ed47d69
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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