2-Chloro-N-MethylethanaMine Hydrochloride Chemical Properties

Melting point:

89 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

White to off-white

InChI

InChI=1S/C3H8ClN.ClH/c1-5-3-2-4;/h5H,2-3H2,1H3;1H

InChIKey

FGSHJLJPYBUBHO-UHFFFAOYSA-N

SMILES

C(NC)CCl.Cl

EPA Substance Registry System

Ethanamine, 2-chloro-N-methyl-, hydrochloride (4535-90-4)

Safety Information

HS Code 

2921199990

2-Chloro-N-MethylethanaMine Hydrochloride Usage And Synthesis

Uses

2-Chloro-N-methylethanamine Hydrochloride is used in the preparation of pyrimidine derivatives and related heterocycles as CDK inhibitors for treatment of diseases.

Uses

2-Chloro-N-Methylethanamine Hydrochloride is an aminoalkoxyimino derivative used in the preparation of amino derivatives of B-homoandrostanes and B-heteroandrostanes for the treatment of cardiovascular disorders.

Synthesis

Example 2: General procedure for the synthesis of 2-chloro-N-methylethylamine hydrochloride from N-methyl-2-hydroxyethylamine 1. Dry hydrogen chloride gas was passed into a solution of dichloromethane (25 ml) containing 2-(methylamino)ethanol (10 g, 133 mmol) under stirring conditions until the mixture turned wet litmus paper red. 2. The reaction mixture was cooled to 0 °C and thionyl chloride (15.82 g, 133 mmol) was added slowly and dropwise. 3. After the dropwise addition was completed, the reaction mixture was stirred at room temperature overnight. 4. After completion of the reaction, the solvent was removed by distillation under reduced pressure to afford the target product 2-chloro-N-methylethylamine hydrochloride as a white solid (16.60 g, 96% yield). Product characterization: melting point 95°-100°C; 1H NMR (DMSO-d6) δ 4.00 (t, 2H, J = 6.28Hz), 3.36 (t, 2H, J = 6.29Hz), 2.81 (s, 3H); IR (KBr) ν 3400, 2960, 2750, 2420, 1730, 1580, 1460, 1390, 1310, 1270, 1200, 1310, 1270, 1200, 1390, 1390. 1310, 1270, 1200, 1150, 1165, 1005, 990, 900, 860, 710 cm-1.

References

[1] Journal of Medicinal Chemistry, 1995, vol. 38, # 14, p. 2672 - 2680
[2] Patent: US5233031, 1993, A
[3] Chemical and Pharmaceutical Bulletin, 2002, vol. 50, # 7, p. 941 - 959
[4] Journal of the Chemical Society. Dalton Transactions, 2001, # 8, p. 1306 - 1318
[5] Journal of medicinal chemistry, 1992, vol. 35, # 17, p. 3246 - 3253

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