4,4-Diethoxy-N,N-dimethyl-1-butanamine Chemical Properties

Boiling point:

194-195C

Density 

0.844 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.421(lit.)

Flash point:

158 °F

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate

form 

Oil

pka

9.71±0.28(Predicted)

color 

Colourless to Pale Yellow

InChI

InChI=1S/C10H23NO2/c1-5-12-10(13-6-2)8-7-9-11(3)4/h10H,5-9H2,1-4H3

InChIKey

QKXMWBLNSPNBEY-UHFFFAOYSA-N

SMILES

C(N(C)C)CCC(OCC)OCC

CAS DataBase Reference

1116-77-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

41-34-10-36/37/38

Safety Statements 

26-36/37/39-16-37

RIDADR 

UN 3267 8 / PGIII

WGK Germany 

3

HS Code 

29225090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4,4-Diethoxy-N,N-dimethyl-1-butanamine Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

4,4-Diethoxy-N,N-dimethyl-1-butanamine is used in organic synthesis and pharmaceutical intermediates, it is an intermediate for Sumatriptan, Rizatriptan, Almotriptan, Zolmitriptan.

Application

4-Dimethylaminobutyraldehyde Diethyl Acetal (Zolmitriptan USP Related Compound H) is used in the preparation of N,N-Dimethyltryptamines, 5-HT1D receptor agonists, for medicinal treatments such as antimigraine drugs.

Preparation

4-Dimethylaminobutyraldehyde diethyl acetal synthesis: The reaction of 1-bromo-3-chloro propane and dimethylamine solution with PEG as a phase transfer catalyst, and obtained 3-dimethylamino-1-chloro propane. 3-dimethylamino-1-chloro propane reacted with magnesium and Grinard reagent was acquired. 4-Dimethylaminobutyraldehyde diethyl acetal is obtained by the reaction of Grinard reagent and triethyl orthoformate. The yield was 70.11%.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 2401, 1994 DOI: 10.1016/0040-4039(94)85230-8

Synthesis

Magnesium shavings (25 g) were added to a 2L four-necked round-bottomed flask under nitrogen protection. Benzene (50 mL), benzene solution of 3-chloro-1-(N,N-dimethyl)propylamine (50 mL), triethyl orthoformate (20 g), and a small amount of iodine crystals were added sequentially and slowly heated to reflux temperature. After 15-20 minutes of refluxing, a vigorous reaction was observed, indicating the onset of the Grignard reaction. The remaining benzene solution of 3-chloro-1-(N,N-dimethyl)propylamine and triethyl orthoformate (174 g, where R3 = R5 = Et) were loaded into two charging funnels and added slowly and dropwise to the reaction mixture over a period of 3-4 hr, maintaining reflux. After completion of the reaction, it was cooled to 25 °C and filtered through a diatomaceous earth pad. The filter cake was washed with benzene (100 mL). Benzene was removed by distillation at atmospheric pressure using a 20 cm Vigreux column. The residue was distilled under mild vacuum with a controlled bath temperature below 100 °C to recover excess triethyl orthoformate (60 g). Finally, 4-dimethylaminobutyraldehyde diethyl acetal was purified by reduced pressure distillation to give 125 g (75.8% yield) of a colorless liquid with a boiling point of 140-150°C/15-20 mmHg.

References

[1] Patent: WO2003/101931, 2003, A2. Location in patent: Page 14-15
[2] Patent: WO2003/101931, 2003, A2. Location in patent: Page 15-16
[3] Patent: WO2004/99141, 2004, A1. Location in patent: Page 9-10

4,4-Diethoxy-N,N-dimethyl-1-butanamine(1116-77-4)Related Product Information

• 2,2-Diethoxyethylamine
• Bromoacetaldehyde diethyl acetal
• Diethyl malonate
• Dacthal
• Dimethyl carbonate
• Dimethyl sulfate
• Ethylene glycol diethyl ether
• ETHANE
• Diethyl oxalate
• Dimethyl ether
• Dimethyl fumarate
• POLY(VINYL BUTYRAL)
• Mefenpyr-diethyl
• N,N-Dimethylformamide
• Dimethyl disulfide
• Metformin
• Acetal
• Dimethyl phthalate