Hydrochloric Acid → Ethyl 2-[2-aminoethyl(methyl)amino]acetate;dihydrochloride

HRID 1777940Notes

Reaction equation

HRID 1777940 reaction equation
[ClH:1].C(OC([NH:9][CH2:10][CH2:11][N:12]([CH3:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)(C)(C)C>C1COCC1.CCO>[ClH:1].[ClH:1].[NH2:9][CH2:10][CH2:11][N:12]([CH3:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 87241117Ethyl N-(2-((tert-butoxycarbonyl)amino)ethyl)-N-methylglycinate2×

Product 1

HCID 22270088Ethyl 2-[2-aminoethyl(methyl)amino]acetate;dihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (10 ml) was added to a solution of ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)(methyl)amino)acetate (intermediate 83, 3.05 g, 11.13 mmol) in THF (20 ml) and EtOH (100 ml) at room temperature. After stirring 1 h at room temperature the reaction mixture was evaporated, ethanol (20 ml) added, evaporated, further ethanol (50 ml) added and then stirred at 60° C. for 70 min. The cooled reaction mixture was then evaporated to give the title compound as a pale-yellow glass. 1H NMR (400 MHz, DMSO-d6) δ 8.58 (s, br, 3H), 4.19 (q, 2H), 4.26-4.15 (m, 2H), 3.44 (s, br, 2H), 3.21 (s, br, 2H), 2.88 (s, 3H), 1.21 (t, 3H).

Workup

  1. customwas evaporated
  2. additionethanol (20 ml) added
  3. customevaporated
  4. additionfurther ethanol (50 ml) added
  5. stirringstirred at 60° C. for 70 min
  6. customThe cooled reaction mixture
  7. customwas then evaporated

Sources & evidence

ORD record
ord-fb85a2d80ae8401db9109bc04c2786d9
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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