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

HRID 1665798

反応式

HRID 1665798 の反応式
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]

参加物

8

反応物 5

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

生成物 1

HCID 534190393-((Dimethylamino)methyl)-5-methyl-2-hexanone収率 16%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-86428a6221074dd6b4cd608150d4bbf0
出典データセット
uspto-grants-2011_10
特許番号
US08039627B2

関連ノート

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