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

HRID 1467719Notes

Reaction equation

HRID 1467719 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-b87c585fc551430cb0240ff88cfced65
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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