Glycinamide hydrochloride → HCID 11324179, compound

HRID 274919Notes

Reaction equation

HRID 274919 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[C:7]([BH3-])#N.[Na+].Cl[C:12]1[C:13]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([CH:17]=[CH:18][CH:19]=1)C=O>CO>[Cl:1][C:26]1[CH:27]=[C:22]([CH:23]=[CH:24][CH:25]=1)[CH2:21][O:20][C:13]1[CH:12]=[CH:19][C:18]([CH2:7][NH:2][CH2:3][C:4]([NH2:6])=[O:5])=[CH:17][CH:14]=1

Participants

5

Reactant 3

HCID 2723639Glycinamide hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 54026983HCID 54026983, compound

Product 1

HCID 11324179HCID 11324179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22.4 g (0.203 mol) of glycinamide hydrochloride are suspended in 1000 ml of dry methanol and 10.2 g (0.162 mol) of sodium cyanoborohydride are added while stirring under nitrogen. After solubilization of the mixture, 50 g (0.203 mol) of 3-chlorobenzyloxybenzaldehyde are added in a single portion. The reaction mixture is stirred 8 hours at room temperature and then allowed to stand 16 hours. The solution is filtered and evaporated, taken up with water and extracted three times with methylene chloride. After drying and evaporating, the crude residue is chromatographed on silica gel (eluant: chloroform/methanol/conc. NH4OH; 97/3/0.3) to give 2-[4-(3-chlorobenzyloxy)benzyl]aminoacetamide which by reaction with the stoichiometric amount of gaseous HCl in ethanol is transformed into its hydrochloride (32.1 g, 46.3%, m.p.: 225°-230° C.).

Workup

  1. stirringThe reaction mixture is stirred 8 hours at room temperature
  2. filtrationThe solution is filtered
  3. customevaporated
  4. extractionextracted three times with methylene chloride
  5. customAfter drying
  6. customevaporating
  7. customthe crude residue is chromatographed on silica gel (eluant: chloroform/methanol/conc. NH4OH; 97/3/0.3)

Sources & evidence

ORD record
ord-07a2be9444b046b49e606272b265e802
Source dataset
uspto-grants-1995_02
Patent number
US05391577

Reaction notes

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