Sodium cyanoborohydride → 5-Chloro-2-(1-isopropylpiperidin-4-ylmethyl-amino)-n-(2pyridyl)benzamide

HRID 49854Notes

Reaction equation

HRID 49854 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:8].CO.[C:27](O)(=O)[CH3:28].[C:31]([BH3-])#N.[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:17][CH2:18][CH:19]2[CH2:20][CH2:21][N:22]([CH:27]([CH3:28])[CH3:31])[CH2:23][CH2:24]2)=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 10129899Acetic acid methanolHCID 120968655-Chloro-2-(piperidin-4-ylmethylamino)-n-(2-pyridyl)benzamide

Product 1

HCID 120965705-Chloro-2-(1-isopropylpiperidin-4-ylmethyl-amino)-n-(2pyridyl)benzamideYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-chloro-2-(piperidin-4-ylmethylamino)-N-(2-pyridyl)benzamide from above (1.3 g, 3.7 mmol) in acetone (28 mL) and methanol-acetic acid (95:5) (12 mL) was treated with sodium cyanoborohydride (1.0 g, 15.0 mmol). Gas evolution was observed; the reaction mixture was then stirred at room temperature for 7 h, after which it was concentrated in vacuo to a residue that was purified via silica gel chromatography. Elution with dichloromethane—2 M ammonia in methanol (9:1) provided 0.5 g (34%)of the title compound as a yellow solid.

Workup

  1. concentrationafter which it was concentrated in vacuo to a residue that
  2. customwas purified via silica gel chromatography
  3. washElution with dichloromethane—2 M ammonia in methanol (9:1)

Sources & evidence

ORD record
ord-8583cdbb2c104f2c95670b61c35f0d11
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Reaction notes

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