Water → tert-Butyl (3-(2-dimethylamino-ethoxy)-4-methyl-phenyl)-carbamate

HRID 914962Notes

Reaction equation

HRID 914962 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH3:8].Cl.[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21]Cl.C([O-])([O-])=O.[K+].[K+].O>COCCOC.CCOC(C)=O>[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][O:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 44668374tert-butyl N-(3-hydroxy-4-methylphenyl)carbamate

Product 1

HCID 71166994tert-Butyl (3-(2-dimethylamino-ethoxy)-4-methyl-phenyl)-carbamate

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7 (2.16 g, 9.68 mmol), 2-(dimethylamino)-ethyl chloride hydrochloride (1.53 g, 10.6 mmol) and K2CO3 (5.35 g, 3.87 mmol) in DME (28 mL)/H2O (7 mL) was heated under reflux overnight. After cooling to room temperature, the solution was diluted with EtOAc (100 mL) and the resulting solution was washed with H2O (2×100 mL) and brine (100 mL).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. washthe resulting solution was washed with H2O (2×100 mL) and brine (100 mL)

Sources & evidence

ORD record
ord-1a8e4aa02f014da6aafcb36c5f97e6cb
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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