Triethylamine → N-[2-(2-Fluorobenzyloxy)-ethoxy]-phthalimide

HRID 234877Notes

Reaction equation

HRID 234877 reaction equation
C(N(CC)CC)C.Br[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19].[OH:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31]>CN1CCCC1=O>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][O:11][CH2:10][CH2:9][O:20][N:21]1[C:22](=[O:31])[C:23]2=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]2[C:25]1=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 233530971-Bromo-2-(2-fluorobenzyloxy)-ethane

Product 1

HCID 23353096N-[2-(2-Fluorobenzyloxy)-ethoxy]-phthalimideYield 82%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

108 ml of triethylamine were added dropwise to a mixture of 165 g (0.71 mol) of 1-bromo-2-(2-fluorobenzyloxy)-ethane, 116 g (0.7 mol) of N-hydroxyphthalimide and 710 ml of N-methyl-2-pyrrolidone at from 20° to 25° C. in the course of 1 hour. After 5 hours at 60° C. the cold reaction mixture was poured into 200 ml of ice water and the precipitate was filtered off under suction, washed with water and isopropanol and dried under reduced pressure over phosphorus pentoxide. Yield: 82%; mp.: 62°-64° C.

Workup

  1. customAfter 5 hours at 60° C. the cold reaction mixture
  2. filtrationthe precipitate was filtered off under suction
  3. washwashed with water and isopropanol
  4. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-10e77219ba014318ab6b6f4538433549
Source dataset
uspto-grants-1997_01
Patent number
US05597776

Reaction notes

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