Toluene → HCID 11389458, compound

HRID 858919Notes

Reaction equation

HRID 858919 reaction equation
[I-].[K+].[Cu][C:4]#[N:5].FC1C=CC([CH:13]2[C:21]3[C:16](=[CH:17][C:18](Br)=[CH:19][CH:20]=3)[CH2:15][O:14]2)=CC=1.C1(C)C=CC=CC=1>CN(C)C=O.N>[CH2:13]1[C:21]2[C:16](=[CH:17][C:18]([C:4]#[N:5])=[CH:19][CH:20]=2)[CH2:15][O:14]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 4875Potassium IodideHCID 113238195-Bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuranHCID 178418546HCID 178418546, compound

Product 1

HCID 11389458HCID 11389458, compoundYield 133.3%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium iodide (25 g), Copper (I) cyanide (11.8 g) were added to a solution of the [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-bromoisobenzofuran (25 g) in dimethylformamide (25 ml). The reaction mixture was heated to 135–145° C. and maintained for 28 hours. The reaction mixture was cooled to 100° C. and poured in ammonia solution containing toluene and stirred for 2 hours to get a clear separation of layers. Then the organic layer after acid base treatment was separated and washed with water twice (2×100 ml), dried with anhydrous sodium sulfate and finally the toluene layer was distilled to get the crude 1-[3-(dimethylamino) propyl]-14-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile base 16.5 g, with the following HPLC profile.

Workup

  1. temperatureThe reaction mixture was heated to 135–145° C.
  2. temperaturemaintained for 28 hours
  3. customto get
  4. customa clear separation of layers
  5. customThen the organic layer after acid base treatment was separated
  6. washwashed with water twice (2×100 ml)
  7. dry with materialdried with anhydrous sodium sulfate
  8. distillationfinally the toluene layer was distilled

Sources & evidence

ORD record
ord-d83a6ea7a95c42479fc8d7cb56d57e54
Source dataset
uspto-grants-2006_12
Patent number
US07148364B2

Reaction notes

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