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

A mixture of 1-(4-(diethoxymethyl)benzaldehyde (2.08 g, 10 mmol) and dimethylamine (33% aqueous solution, 2.74 g, 20 mmol) in methanol (20 mL) was stirred at room temperature for 40 mins. The mixture was cooled to 0° C., sodium borohydride (0.57 g, 15 mmol) was added portionwise. After the addition, the mixture was stirred at room temperature for 4 hr. Methanol was removed under reduced pressure. The residue was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic layer was separated. The aqueous layer was extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 1-(4-(diethoxymethyl)phenyl)-N,N-dimethylmethanamine (1.8 g) as a light yellow oil which was used in the next step without further purification. MS (ESI) m/z: 237 (M+1)+.

1. temperatureThe mixture was cooled to 0° C.
2. additionAfter the addition
3. stirringthe mixture was stirred at room temperature for 4 hr
4. customMethanol was removed under reduced pressure
5. customThe residue was partitioned between water (50 mL) and ethyl acetate (50 mL)
6. customThe organic layer was separated
7. extractionThe aqueous layer was extracted with ethyl acetate (50 mL×3)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated

ORD record

ord-fbd7d9c798634a29b277e695bc2a2afa

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420650B2