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

HRID 1665798

반응식

HRID 1665798 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-86428a6221074dd6b4cd608150d4bbf0
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039627B2

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