ChemicalBook CAS DataBase List N,N-Dimethylglycine

N,N-Dimethylglycine synthesis

13synthesis methods

Product Name:N,N-Dimethylglycine
CAS Number:1118-68-9
Molecular formula:C4H9NO2
Molecular Weight:103.12

N,N-Dimethylglycine is commercially available as the free form amino acid, and as the hydrochloride salt [2491-06-7 ]. DMG may be prepared by the alkylation of glycine via the Eschweiler–Clarke reaction. In this reaction, glycine is treated with aqueous formaldehyde in formic acid that serves as both solvent and reductant. Hydrochloric acid is added thereafter to give the hydrochloride salt. The free amino acid may been obtained by neutralization of the acid salt, which has been performed with silver oxide.
H₂NCH₂COOH + 2 CH₂O + 2 HCOOH →(CH₃)₂NCH₂COOH + 2 CO₂ + 2 H₂O.

67-56-1 Synthesis

67-56-1
757 suppliers
$9.00/25ml

56-40-6 Synthesis

56-40-6
1242 suppliers
$5.00/25g

1118-68-9
387 suppliers
$7.00/1g

Yield:1118-68-9 100 %

Reaction Conditions:

with C₂₆H₃₇Cl₂IrN₃⁽²⁺⁾*2C₂F₆NO₄S₂^(1-) in 2,2,2-trifluoroethanol at 50;

Steps:

General Procedure B

General procedure: Iridium complex 11 (3.2 mg, 0.005 mmol, 1 equiv.) and silver salt AgNTf2 (4.2 mg, 0.011 mmol, 2.1 equiv.)were suspended in anhydrous dichloromethane (1 mL), in a vial covered in aluminum foil. The reaction mixturewas stirred at room temperature for 15 minutes. The mixture was filtered off through a pad of Celite to removethe AgCl precipitated, and transferred to an oven dried pressure tube. The solvent was evaporated under vacuumand the active catalyst species used in-situ.The pressure tube impregnated with the active iridium species Ir-4- NTf2 (0.005 mmol, 2 mol%) was loadedwith dry TFE (1 mL). The corresponding amino acid (0.25 mmol, 1 equiv.) and methanol (0.1 mL) were addedand the mixture was stirred at 50 °C overnight. The crude was then cooled down to r.t., dried under vacuum, andwashed with diethyl ether (3x3 mL) to remove the excess of alcohol and the catalyst. Quantitative isolated yieldswere obtained in all substrates without the need of any further workup or purification (Scheme S5).

References:

Bermejo-López, Aitor;Raeder, Majken;Martínez-Castro, Elisa;Martín-Matute, Belén [Chem,2022,vol. 8,# 12,p. 3302 - 3323] Location in patent:supporting information

50-00-0 Synthesis