Hydrochloric Acid → HCID 131718077, compound

HRID 274920Notes

Reaction equation

HRID 274920 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][O:7][C:8]1([O:15][CH2:16][CH3:17])[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH2:9]1.Cl[CH2:22][C:23]([NH2:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][O:7][C:8]1([O:15][CH2:16][CH3:17])[CH:9]=[CH:10][C:11]([NH:14][CH2:22][C:23]([NH2:25])=[O:24])=[CH:12][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 70080169HCID 70080169, compound

Product 1

HCID 131718077HCID 131718077, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

31 g (0.104 mol) of 4-(3-chlorobenzyloxy)phenetylamine hydrochloride are suspended in 450 ml of anhydrous ethanol. To this mixture, 9.7 g (0.104 mol) of chloroacetamide and 28.8 g (0.208 mol) of anhydrous potassium carbonate are added. After heating to reflux, stirring is continued for 40 hours. The hot mixture is filtered, then evaporated to dryness and the crude residue chromatographed on silica gel (eluant CHCl3/MeOH/conc. NH4OH; 97/3/0.3). The free compound obtained (20.2 g; 60.7%) is treated with gaseous HCl in ethanol to give a quantitative yield of the corresponding [4-(3-chlorobenzyloxy)phenetyl]aminoacetamide, hydrochloride, m.p. 248°-251° C. Analogously the following compound can be obtained, starting from the corresponding primary amine:

Workup

  1. temperatureAfter heating
  2. temperatureto reflux
  3. filtrationThe hot mixture is filtered
  4. customevaporated to dryness
  5. customthe crude residue chromatographed on silica gel (eluant CHCl3/MeOH/conc. NH4OH; 97/3/0.3)
  6. customThe free compound obtained (20.2 g; 60.7%)

Sources & evidence

ORD record
ord-7d1ad076563a42b7b35b386f296a25e3
Source dataset
uspto-grants-1995_02
Patent number
US05391577

Reaction notes

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