2-(1-Boc-piperidin-4-ylmethylamino)-5-chloro-n-(2-pyridyl)benzamide → 5-Chloro-2-(piperidin-4-ylmethylamino)-n-(2-pyridyl)benzamide

HRID 49853Notes

Reaction equation

HRID 49853 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:19])[CH2:10][CH2:9]1)(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[Cl:31][C:28]1[CH:29]=[CH:30][C:16]([NH:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[C:17]([CH:27]=1)[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)=[O:19]

Participants

3

Reactant 1

HCID 120968642-(1-Boc-piperidin-4-ylmethylamino)-5-chloro-n-(2-pyridyl)benzamide

Product 1

HCID 120968655-Chloro-2-(piperidin-4-ylmethylamino)-n-(2-pyridyl)benzamideYield 89%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(1-Boc-piperidin-4-ylmethylamino)-5-chloro-N-(2-pyridyl)benzamide (6.1 g, 14 mmol) in trifluoroacetic acid (125 mL) was stirred at 70° C. for 2 h, then at room temperature for 24 h. The solution was concentrated in vacuo, and the residue was directly applied to a silica gel column. Elution with dichloromethane—2 M ammonia in methanol (9:1) afforded 4.2 g (89%) of the pure title compound as a yellow solid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washElution with dichloromethane—2 M ammonia in methanol (9:1)

Sources & evidence

ORD record
ord-2287ebe6058e4ccd9e811f5f0b76b515
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Reaction notes

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