2-(Methylamino)ethanol → HCID 974060, compound

HRID 1170474Notes

Reaction equation

HRID 1170474 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[CH2:6]1[O:16][C:15]2[CH:14]=[CH:13][C:10]([CH2:11]Cl)=[CH:9][C:8]=2[O:7]1>C(Cl)Cl>[O:16]1[C:15]2[CH:14]=[CH:13][C:10]([CH2:11][N:2]([CH3:1])[CH2:3][CH2:4][OH:5])=[CH:9][C:8]=2[O:7][CH2:6]1

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 974060HCID 974060, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(Methylamino)ethanol (22.0 g, 290 mmol) is added all at once to a stirred solution of 3,4-methylenedioxybenzyl chloride (25.0 g, 147 mmol) in DCM (45 mL) at −78° C. under nitrogen. The solution is stirred for 15 minutes at −78° C. then allowed to warm to room temperature overnight (16 h). The reaction is quenched with 1.2 M NaOH (100 mL), washed twice with water, dried of MgSO4, and filtered. Concentration under reduced pressure afforded 25.3 g (83%) of 2-(benzo[1,3]dioxol-5-ylmethyl-methyl-amino)-ethanol as a clear oil which was suitable for use in the next step.

Workup

  1. temperatureto warm to room temperature overnight (16 h)
  2. customThe reaction is quenched with 1.2 M NaOH (100 mL)
  3. washwashed twice with water
  4. dry with materialdried of MgSO4
  5. filtrationfiltered
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-69d60011e66d4c21a70f968637423c01
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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