1,2-Ethanediamine, N1,N1,N2-trimethyl- → 2-Benzyloxy-N-(2-(dimethylamino)ethyl)-N-methylacetamide

HRID 1397130Notes

Reaction equation

HRID 1397130 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][NH:5][CH3:6].[CH2:8]([O:15][CH2:16][C:17](Cl)=[O:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[CH2:8]([O:15][CH2:16][C:17]([N:5]([CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])[CH3:6])=[O:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 177085Benzyloxyacetyl chloride

Product 1

HCID 669739782-Benzyloxy-N-(2-(dimethylamino)ethyl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N,N,N′-Trimethylethylenediamine (99, 0.17 mL, 1.308 mmol) was dissolved in 5 mL of dichloromethane and cooled to 0° C. in an ice-water bath. 2-Benzyloxyacetyl chloride (100, 0.2 mL, 1.267 mmol) was added to the above solution dropwise and the mixture was allowed to warm to room temperature. After overnight, the reaction was complete and the mixture was concentrated and used in the next step without purification as HCl salt: 1H NMR (400 MHz, CDCl3): δ 2.86 (s, 3H), 2.87 (s, 3H), 3.09 (s, 3H), 3.16 (q, J=5.5, 2H), 3.85 (t, J=6.6, 2H), 4.24 (s, 2H), 4.63 (s, 2H), 7.30-7.39 (m, 5H).

Workup

  1. temperatureto warm to room temperature
  2. concentrationthe mixture was concentrated
  3. customused in the next step without purification as HCl salt

Sources & evidence

ORD record
ord-ba01a42c8a3b44b2b4e51b4e594fa32e
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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