1,4-Dioxane hydrochloride → N-methyl-4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-N-piperidin-4-ylmethyl-benzamide

HRID 717084Notes

Reaction equation

HRID 717084 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH3:36])[C:16](=[O:35])[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[NH:24][C:25](=[O:34])[C:26]4[C:31]([CH:32]=3)=[C:30]([CH3:33])[CH:29]=[CH:28][CH:27]=4)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[CH3:36][N:15]([CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:16](=[O:35])[C:17]1[CH:18]=[CH:19][C:20]([C:23]2[NH:24][C:25](=[O:34])[C:26]3[C:31]([CH:32]=2)=[C:30]([CH3:33])[CH:29]=[CH:28][CH:27]=3)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 717375334-({Methyl-[4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 117992757N-methyl-4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-N-piperidin-4-ylmethyl-benzamideYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-({methyl-[4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzoyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester (170 mg, 0.35 mmol) in CH2Cl2 (5 mL) was added 4M HCl/dioxane (2 mL) and the reaction mixture stirred at RT for 4 h. The solvent was removed in vacuo and the crude product purified by reverse phase preparative HPLC-MS to obtain N-methyl-4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-N-piperidin-4-ylmethyl-benzamide as a pale orange solid (44 mg, 33%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-2be7e25c9db54c0e9845bda66452953b
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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