Sodium hydride → HCID 58503995, compound

HRID 2407675Notes

Reaction equation

HRID 2407675 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.[H-].[Na+].Br[CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1>CN(C)C=O.C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19][CH2:18]1)[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 193756376-Chloro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 58503995HCID 58503995, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A room temperature solution of 6-chloro-3,4-dihydroisoquinolin-1(2H)-one (0.100 g) in N,N-dimethylformamide (3 mL) was treated with sodium hydride (95% dispersion in mineral oil, 0.028 g) and stirred for 20 minutes. tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate (0.184 g) was added and the reaction was stirred at 40° C. overnight. The mixture was diluted with diethyl ether and washed sequentially with water, 1 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and brine. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=47:3) to obtain the title compound (0.188 g) having the following physical data.

Workup

  1. stirringthe reaction was stirred at 40° C. overnight
  2. washwashed sequentially with water, 1 N hydrochloric acid
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=47:3)

Sources & evidence

ORD record
ord-f1d670e36c184485a2472c3c08d9b8ac
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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