Ammonia → N-[2-(4-Carboethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4yl)morpholine hydrochloride

HRID 477131Notes

Reaction equation

HRID 477131 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([N:15]2[CH2:20][CH2:19][O:18][CH:17]([C:21]3[N:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[S:24][CH:25]=3)[CH2:16]2)[CH3:14])=[CH:8][CH:7]=1)([OH:3])=[O:2].[CH2:30](O)[CH3:31].S(=O)(=O)(O)O.N.C(Cl)(Cl)[Cl:40]>>[ClH:40].[C:1]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([N:15]2[CH2:20][CH2:19][O:18][CH:17]([C:21]3[N:22]=[C:23]([C:26]([F:27])([F:28])[F:29])[S:24][CH:25]=3)[CH2:16]2)[CH3:14])=[CH:8][CH:7]=1)([O:3][CH2:30][CH3:31])=[O:2]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 702EthanolHCID 1118Sulfuric AcidHCID 6212ChloroformHCID 19974278N-[2-(4-Carboxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

Product 1

HCID 19974260N-[2-(4-Carboethoxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4yl)morpholine hydrochloride

Procedure

0.5 g (0.0012 mol) of N-[2-(4-carboxymethoxyphenyl)-1-methylethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine is dissolved in 150 ml of chloroform and, while stirring, 2 ml ethanol and 0.25 g of concentrated sulphuric acid are added, and the the mixture is heated to reflux with a water trap for one hour. The mixture is then cooled, ice-water is added, the mixture is made alkaline with ammonia and the phases are separated. The aqueous phase is then extracted again by shaking with chloroform, and the organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The resulting residue is dissolved in ether, ethereal hydrochloric acid is added, the mixture is evaporated to dryness, and the residue is triturated with acetone and filtered off with suction.

Workup

  1. temperaturethe the mixture is heated
  2. temperatureto reflux with a water trap for one hour
  3. temperatureThe mixture is then cooled
  4. customthe phases are separated
  5. extractionThe aqueous phase is then extracted again
  6. stirringby shaking with chloroform
  7. dry with materialthe organic phase is dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. dissolutionThe resulting residue is dissolved in ether
  11. additionethereal hydrochloric acid is added
  12. customthe mixture is evaporated to dryness
  13. customthe residue is triturated with acetone
  14. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-ccee82d1d7ec447e99862b98e7790397
Source dataset
uspto-grants-1989_12
Patent number
US04886814

Reaction notes

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