Sodium hydride → HCID 178491067, compound

HRID 1846797Notes

Reaction equation

HRID 1846797 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[Cl:29][C:30]1[C:35](Cl)=[N:34][CH:33]=[CH:32][N:31]=1>CN(C=O)C.O>[Cl:29][C:30]1[C:35]([O:17][C@H:14]2[CH2:15][CH2:16][C@H:11]([N:10]([CH2:9][C:8]3[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:28][CH:27]=3)[CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[CH2:12][CH2:13]2)=[N:34][CH:33]=[CH:32][N:31]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 785752,3-DichloropyrazineHCID 178491068HCID 178491068, compound

Product 1

HCID 178491067HCID 178491067, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (0.58 g, 14.5 mmol, 60% dispersion in mineral oil) was added to a solution of trans-4-(bis(4-methoxybenzyl)amino)cyclohexanol (4.30 g, 12.1 mmol) in DMF (50 mL). The mixture was stirred for 30 min at RT before 2,3-dichloropyrazine (1.89 mL, 12.7 mmol) was added dropwise via syringe. The reaction mixture was warmed to 60° C. and stirred overnight. The mixture was diluted with water and extracted with EtOAc (3×). The extracts were combined, washed with water (3×), washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude oil was purified by silica gel chromatography to give trans-4-(3-chloropyrazin-2-yloxy)-N,N-bis(4-methoxybenzyl)cyclohexanamine as a white solid.

Workup

  1. additionwas added dropwise via syringe
  2. extractionextracted with EtOAc (3×)
  3. washwashed with water (3×)
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-70dc50fc9ae54043bd0c81afe014786f
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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