Hydrochloric Acid → HCID 20389796, compound

HRID 426748Notes

Reaction equation

HRID 426748 reaction equation
[C:1]([CH2:3][C:4]1[CH:13]=[C:12]([F:14])[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]=1[F:15])#[N:2].B.[H][H].Cl>O1CCCC1.CO>[NH2:2][CH2:1][CH2:3][C:4]1[CH:13]=[C:12]([F:14])[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]=1[F:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 20389781HCID 20389781, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 20389796HCID 20389796, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

6-Cyanomethyl-5,8-difluoro-1,4-benzodioxane (30.34 g, 0.158 mole) dissolved in 300 ml of dry tetrahydrofuran is treated with 308 ml of 1 M borane in tetrahydrofuran under nitrogen. After 2 hours of reflux 300 ml of methanol is added continuously (hydrogen evolution occurs, vigorously at first), then the mixture is refluxed for 30 minutes. Then 50 ml of 10% hydrochloric acid is added very carefully (hydrogen gas evolution again) and the mixture refluxed another 30 minutes. The reaction mixture is concentrated under vacuum to a small volume, then 300 ml of water is added and the mixture made basic with 40% sodium hydroxide. This is extracted with ether, dried, and concentrated to give 6-(2-aminoethyl)-5,8-difluoro-1,4-benzodioxane.

Workup

  1. temperaturevigorously at first), then the mixture is refluxed for 30 minutes
  2. temperaturerefluxed another 30 minutes
  3. concentrationThe reaction mixture is concentrated under vacuum to a small volume
  4. addition300 ml of water is added
  5. extractionThis is extracted with ether
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a817b035da224ba9b4378add8687fd07
Source dataset
uspto-grants-1979_10
Patent number
US04171359

Reaction notes

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