Triethylamine → (3,4-Dichlorophenyl)-(4-{[(6-fluoropyridin-2-ylmethyl)amino]-methyl}piperidin-1-yl)methanone

HRID 376306Notes

Reaction equation

HRID 376306 reaction equation
[F:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[Cl:35])[C:29](Cl)=[O:30].[BH4-].[K+]>C1C=CC=CC=1.O1CCCC1.CO.O>[Cl:25][C:26]1[CH:27]=[C:28]([C:29]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][CH2:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=3)[CH2:12][CH2:11]2)=[O:30])[CH:32]=[CH:33][C:34]=1[Cl:35]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 235274-(Aminomethyl)piperidineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 4192641Potassium borohydrideHCID 106067416-Fluoropyridine-2-carboxaldehyde

Product 1

HCID 10786906(3,4-Dichlorophenyl)-(4-{[(6-fluoropyridin-2-ylmethyl)amino]-methyl}piperidin-1-yl)methanone

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.29 g of 6-fluoropyridine-2-carbaldehyde (2.31 mmol) and 0.264 g of piperidin-4-ylmethylamine (2.31 mmol) are mixed in 20 ml of benzene. The solution is heated under reflux under a nitrogen atmosphere for 2 hours with removal of the water formed continuously. The solvent is evaporated off and the residue is taken up in 2 ml of tetrahydrofuran. The solution obtained is cooled to 0° C., 0.50 ml of triethylamine (3.50 mmol) is added successively and then 0.469 g of 3,4-dichlorobenzoyl chloride (2.24 mmol) diluted in 1 ml of tetrahydrofuran is added dropwise. The mixture is stirred for 2 hours at room temperature. 10 ml of methanol are added followed, in portions, by 0.25 g of potassium borohydride (4.62 mmol). After 4 hours at room temperature, the solvents are evaporated off, the residue is taken up in water and extracted with chloroform. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: chloroform/methanol; 95:5). 0.40 g of a yellow solid is obtained.

Workup

  1. temperatureThe solution is heated
  2. customformed continuously
  3. customThe solvent is evaporated off
  4. customThe solution obtained
  5. additionis added dropwise
  6. waitAfter 4 hours at room temperature
  7. customthe solvents are evaporated off
  8. extractionextracted with chloroform
  9. washThe organic phase is washed with water
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-909a3205f21141e3b5b342d28387b098
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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