Sodium hydride → HCID 86666509, compound

HRID 1426351Notes

Reaction equation

HRID 1426351 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[Cl:17][C:18]1[CH:23]=[C:22]([CH2:24][N:25]([CH3:27])[CH3:26])[CH:21]=[C:20](Cl)[N:19]=1>CN(C=O)C.CO>[Cl:17][C:18]1[N:19]=[C:20]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:21]=[C:22]([CH2:24][N:25]([CH3:27])[CH3:26])[CH:23]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 2781997HCID 2781997, compound

Product 1

HCID 86666509HCID 86666509, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (44.2 mg, 0.219 mmol) in DMF (0.7 mL) was added sodium hydride (13.2 mg, 0.329 mmol). After stirring for 30 minutes, 1-(2,6-dichloropyridin-4-yl)-N,N-dimethylmethanamine (45 mg, 0.22 mmol) was added to the reaction vial. The reaction solution was heated at 100° C. overnight. The reaction solution was diluted with methanol and purified with preparative LCMS to give the desired product. LCMS (M+H)+: 370.1.

Workup

  1. custompurified with preparative LCMS

Sources & evidence

ORD record
ord-9e22a8035929428ca92350ddcd085c1f
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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