Triethylamine → Ethyl 2-chloro-3,4-dimethoxyphenethylcarbamate

HRID 525844Notes

Reaction equation

HRID 525844 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH2:14].C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCl>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH:14][C:23](=[O:24])[O:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 30177522-Chloro-3,4-dimethoxyphenethylamine

Product 1

HCID 86732714Ethyl 2-chloro-3,4-dimethoxyphenethylcarbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 2-(2-chloro-3,4-dimethoxyphenyl)ethanamine (2.8 g, 12.98 mmol) in dichloromethane (DCM) (40 mL) at 0° C. was added triethylamine (1.990 mL, 14.28 mmol) and ethyl chloroformate (1.371 mL, 14.28 mmol). The reaction mixture was stirred at room temperature for 12 hours. The resulting mixture was washed with water, brine, dried over magnesium sulfate and chromatographed to give ethyl 2-chloro-3,4-dimethoxyphenethylcarbamate (1.7 g, 5.91 mmol, 97% yield). LCMS (M+H)+: 288.1

Workup

  1. washThe resulting mixture was washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. customchromatographed

Sources & evidence

ORD record
ord-6d8bc861aceb42b687017dea8e3f2a98
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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