Potassium borohydride → HCID 10647006, compound

HRID 376307Notes

Reaction equation

HRID 376307 reaction equation
[NH2:1][CH2:2][C:3]1([F:19])[CH2:8][CH2:7][N:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([Cl:18])[CH:12]=2)=[O:10])[CH2:5][CH2:4]1.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]1[N:30]=[C:29]([CH:31]=O)[CH:28]=[CH:27][CH:26]=1.[BH4-].[K+]>C1(C)C=CC=CC=1>[Cl:18][C:13]1[CH:12]=[C:11]([C:9]([N:6]2[CH2:7][CH2:8][C:3]([F:19])([CH2:2][NH:1][CH2:31][C:29]3[CH:28]=[CH:27][CH:26]=[C:25]([C:21]4[O:20][CH:24]=[CH:23][CH:22]=4)[N:30]=3)[CH2:4][CH2:5]2)=[O:10])[CH:16]=[CH:15][C:14]=1[F:17]

Participants

5

Reactant 3

HCID 4192641Potassium borohydrideHCID 10517507HCID 10517507, compoundHCID 10749732HCID 10749732, compound

Product 1

HCID 10647006HCID 10647006, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.687 g of (4-aminomethyl-4-fluoropiperidin-1-yl)-(3-chloro-4-fluorophenyl)methanone (2.38 mmol) and 0.371 g of 6-furan-2-yl-pyridine-2-carbaldehyde (2.38 mmol) are mixed in 25 ml of toluene. The solution is heated under reflux under a nitrogen atmosphere for 2 hours, removing the water formed continuously. The toluene is evaporated off, the residue is taken up in 25 ml of methanol and then 0.257 g of potassium borohydride (4.51 mmol) is added in portions. The reaction mixture is stirred for 5 hours at room temperature and then the methanol is evaporated off. The residue is taken up in chloroform, the organic phase is washed with water and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: chloroform/methanol; 98:2). 0-65 g of a yellow oil is obtained.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux under a nitrogen atmosphere for 2 hours
  3. customremoving the water
  4. customformed continuously
  5. customThe toluene is evaporated off
  6. customthe methanol is evaporated off
  7. washthe organic phase is washed with water
  8. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b00debc2713b4e35a0460b675d31c391
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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