Hydrochloric Acid → 3-((Dimethylamino)methyl)-5-methyl-2-hexanone

HRID 1807439

Reaction equation

HRID 1807439 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[CH3:5][CH:6]([CH3:12])[CH2:7][CH2:8][C:9](=[O:11])[CH3:10].[CH2:13]=O.Cl.[OH-].[Na+]>CO.C(Cl)Cl>[CH3:2][N:3]([CH2:13][CH:8]([CH2:7][CH:6]([CH3:12])[CH3:5])[C:9](=[O:11])[CH3:10])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 80345-Methyl-2-hexanoneHCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 534190393-((Dimethylamino)methyl)-5-methyl-2-hexanoneYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Dimethylamine HCl (90 g, 1.1 mol), 5-methyl-2-hexanone (450 mL, 3.3 mol), and paraformaldehyde (50 g, 1.7 mol) were suspended in MeOH (80 mL) and concentrated HCl (200 μL) was added. The reaction mixture was heated to 80° C. for 12 hours. The mixture was allowed to cool to room temperature and 10% NaOH was added until basic. The entire mixture was extracted with Et2O (100 mL, 2×). The organic layer was dried over MgSO4 and concentrated. The crude reaction mixture was columned via flash column chromatography (0.5:9.5 MeOH:CH2Cl2) to give 30 g (175 mmol) of 3-dimethylaminomethyl-5-methyl-hexan-2-one 1a in a 16% yield.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe entire mixture was extracted with Et2O (100 mL, 2×)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude reaction mixture

Sources & evidence

ORD record
ord-1257ce50c23242ca8dfd96ffb43d2319
Source dataset
uspto-grants-2013_01
Patent number
US08357697B2

Linked notes

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