Boron trifluoride etherate → HCID 15101108, compound

HRID 704579Notes

Reaction equation

HRID 704579 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[CH2:15][CH2:14]3)=O)[CH2:8][CH2:7][C:5]=2[N:6]=1.[BH4-].[Na+].B(F)(F)F.CCOCC>O1CCCC1>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[N:16]1[CH2:17][CH2:18][N:13]([CH2:11][CH:9]2[CH2:8][CH2:7][C:5]3[N:6]=[C:2]([NH2:1])[S:3][C:4]=3[CH2:10]2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 15101104HCID 15101104, compound

Product 1

HCID 15101108HCID 15101108, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-1-[(2-amino-4,5,6,7-tetrahydro-6-benzothiazolyl)carbonyl]-4-(2-pyridinyl)-piperazine (2.8 g) (Example 6) in 200 ml of anhydrous tetrahydrofuran is treated with sodium borohydride (1.0 g) under nitrogen. The mixture is cooled in an ice bath and treated with boron trifluoride etherate (3.93 ml) dropwise. The reaction mixture is stirred at room temperature overnight, and quenched with 5 ml of glacial acetic acid. The mixture is evaporated in vacuo and the residue dissolved in 200 ml of a 10% solution of hydrochloric acid and refluxed for about 30 minutes. The solution is cooled in an ice bath and made basic with a concentrated solution of ammonium hydroxide and extracted with chloroform. The organic extract is dried (magnesium sulfate) and evaporated. The residue is triturated with 50 ml of warm diethyl ether and, after cooling to room temperature, is filtered. The title compound is obtained as a colorless solid; mp 177°-179° C.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. customquenched with 5 ml of glacial acetic acid
  3. customThe mixture is evaporated in vacuo
  4. dissolutionthe residue dissolved in 200 ml of a 10% solution of hydrochloric acid
  5. temperaturerefluxed for about 30 minutes
  6. temperatureThe solution is cooled in an ice bath
  7. extractionextracted with chloroform
  8. extractionThe organic extract
  9. dry with materialis dried (magnesium sulfate)
  10. customevaporated
  11. customThe residue is triturated with 50 ml of warm diethyl ether
  12. temperatureafter cooling to room temperature
  13. filtrationis filtered

Sources & evidence

ORD record
ord-f2fd22cd0dc046dbb376c1df0018af13
Source dataset
uspto-grants-1991_01
Patent number
US04988699

Reaction notes

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