Dimethylamine → 1-(4-(Diethoxymethyl)phenyl)-n,n,-dimethylmethanamine

HRID 1467719ノート

反応式

HRID 1467719 の反応式
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH3:2].[CH3:16][NH:17][CH3:18].O.[BH4-].[Na+]>CO>[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:17]([CH3:18])[CH3:16])=[CH:7][CH:6]=1)[CH3:2]

参加物

6

反応物 4

HCID 674DimethylamineHCID 962WaterHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 230003481-(4-(Diethoxymethyl)phenyl)-n,n,-dimethylmethanamine収率 90%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 4-(diethoxymethyl)benzaldehyde (6.8 g, 32.69 mmol) and dimethylamine in 33 wt. % solution in water (9.25 g, 98 mmol) in methanol (200 mL) was stirred at room temperature for overnight. Sodium borohydride (1.85 g, 49 mmol) was added by portions with ice cooling. After the addition, the mixture was stirred at room temperature for 4 hr. The mixture was quenched with water (100 mL) and extracted with ethyl acetate (100 ml×3). The extract was dried over anhydrous sodium sulfate and concentrated to give crude title compound (7.0 g, yield 90%), which was used in the next step without further purification. LC-MS (ESI) m/z: 238 (M+1)+.

後処理

  1. additionAfter the addition
  2. customThe mixture was quenched with water (100 mL)
  3. extractionextracted with ethyl acetate (100 ml×3)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-b87c585fc551430cb0240ff88cfced65
出典データセット
uspto-grants-2015_04
特許番号
US08999987B2

反応ノート

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