Water → 4-(Methylamino)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine

HRID 2300305Notes

Reaction equation

HRID 2300305 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:27][NH2:28].O>ClCCCl.C(O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[CH3:27][NH:28][CH:23]1[CH2:24][CH2:25][N:20]([CH2:19][C:17]2[CH:16]=[CH:15][N:14]=[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:18]=2)[CH2:21][CH2:22]1

Participants

7

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 22557811[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl-4-piperidone

Product 1

HCID 225578504-(Methylamino)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolventHCID 5049666Sodium triacetoxyborohydrideSolvent

Procedure

To a solution of 1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-4-piperidone (1.00 g) in 1,2-dichloroethane (60 mL) was added 30% solution of methylamine in ethanol (750 mg) and sodium triacetoxyborohydride (1.66 g). The mixture was stirred at room temperature for 3 hours, then small amount of water was added and evaporated. Water was added to the residue and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was subjected to silica gel column chromatography using chloroform-methanol (40:1) to give the title compound.

Workup

  1. customevaporated
  2. additionWater was added to the residue
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0ad95331cf104919bdac1ae310f493bf
Source dataset
uspto-grants-2002_12
Patent number
US06498169B1

Reaction notes

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