3-Fluoro-4-morpholinoaniline → (2R)-1-Chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-2-propanol

HRID 18665

Reaction equation

HRID 18665 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[NH2:5].[CH2:15]1[O:17][C@H:16]1[CH2:18][Cl:19]>C(O)(C)C>[Cl:19][CH2:18][C@H:16]([OH:17])[CH2:15][NH:5][C:4]1[CH:6]=[CH:7][C:8]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 14853303-Fluoro-4-morpholinoanilineHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 16655948(2R)-1-Chloro-3-[[3-fluoro-4-(4-morpholinyl)phenyl]amino]-2-propanolYield 99.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Fluoro-4-morpholinyl aniline (39 g) is mixed with R-epichlorohydrin (18.5 g), isopropyl alcohol (200 ml) is added and heated for 16 hours at reflux temperature. The solvent is distilled to give 57 gm of N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline.

Workup

  1. additionis added
  2. temperatureheated for 16 hours
  3. temperatureat reflux temperature
  4. distillationThe solvent is distilled

Sources & evidence

ORD record
ord-be059e33dcdc4ec49c1e9eb1e2a24b02
Source dataset
uspto-grants-2010_06
Patent number
US07741480B2

Linked notes

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