1,1-Dimethylethyl N-[2-[(4-chlorobenzoyl)amino]ethyl]carbamate → N-(2-Aminoethyl)-4-chlorobenzamide hydrochloride

HRID 2255102Notes

Reaction equation

HRID 2255102 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C)=[O:7])=[CH:4][CH:3]=1>C(O)=O>[ClH:1].[NH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

3

Reactant 1

HCID 135768931,1-Dimethylethyl N-[2-[(4-chlorobenzoyl)amino]ethyl]carbamate

Product 1

HCID 5702251N-(2-Aminoethyl)-4-chlorobenzamide hydrochlorideYield 190.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2.8 g of t-butyl [2-(4-chlorobenzamido)ethyl]carbamate in 50 ml of formic acid is left to stand at room temperature for 1.5 hours. The mixture is then concentrated to dryness, and the residue is dissolved in 50 ml of hydrochloric acid(l:l; volume/volume). The solution is concentrated, the residue is evaporated twice with ethanol/benzene and then recrystallized from ethanol. There are obtained 2.1 g of N-(2-aminoethyl)-4-chlorobenzamide hydrochloride which is identical with the product obtained in Example 1.

Workup

  1. concentrationThe mixture is then concentrated to dryness
  2. dissolutionthe residue is dissolved in 50 ml of hydrochloric acid(l:l; volume/volume)
  3. concentrationThe solution is concentrated
  4. customthe residue is evaporated twice with ethanol/benzene
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-efdf32f9ee6c4804ab65832f207c47f4
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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