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| | 4,4-Diethoxy-N,N-dimethyl-1-butanamine Basic information |
| Product Name: | 4,4-Diethoxy-N,N-dimethyl-1-butanamine | | Synonyms: | N,N-DIMETHYL-4-AMINOBUTANAL DIETHYL ACETAL;N, N-DIMETHYL-4,4-DIETHOXY-1-BUTANAMINE;Zolmitriptan Related Compound H;4-(N,N-DIMETHYLAMINO)BUTANAL DIETHYL ACETAL;4-DIMETHYLAMINO BUTANAL DIETHYL ACETAL;(4,4-DIETHOXY-BUTYL)-DIMETHYL-AMINE;4,4-DIETHOXY-N,N-DIMETHYL-1-BUTANAMINE;4,4-DIETHOXY-N,N-DIMETHYLBUTANAMINE | | CAS: | 1116-77-4 | | MF: | C10H23NO2 | | MW: | 189.3 | | EINECS: | 601-109-1 | | Product Categories: | Other Products;API intermediates;Amines;Intermediates of Rizatriptan | | Mol File: | 1116-77-4.mol |  |
| | 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.) | | Fp | 158 °F | | storage temp. | 2-8°C | | solubility | Chloroform, Ethyl Acetate | | form | Oil | | pka | 9.71±0.28(Predicted) | | color | Colourless to Pale Yellow | | Major Application | pharmaceutical (small molecule) | | 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) |
| 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 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Eye Dam. 1 |
| | 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 Preparation Products And Raw materials |
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