Dimethylamine → HCID 131718078, compound

HRID 2254685Notes

Reaction equation

HRID 2254685 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][NH:12][CH2:13][C:14](OCC)=[O:15])=[CH:9][CH:8]=1.[CH3:24][NH:25][CH3:26]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][NH:12][CH2:13][C:14]([N:25]([CH3:26])[CH3:24])=[O:15])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 10830513HCID 10830513, compound

Product 1

HCID 131718078HCID 131718078, compoundYield 23%

Procedure

7.07 g (0.066 mol) of glycine ethyl ester, hydrochloride are diluted in 200 ml of dry methanol and 3.32 g (0.053 mol) of sodium cyanoborohydride are added, while stirring under nitrogen. To this solution, 15 g (0.0608 mol) of 3-chlorobenzyloxybenzaldehyde are added in a single portion. Stirring is continued for 18 hours at room temperature, the mixture is evaporated to dryness and the crude residue chromatographed on silica gel (eluant: cyclohexane/ethyl acetate; 60/40). 6.8 g (34%) of [4-(3-chlorobenzyloxy)benzyl]amino acetic acid, ethyl ester are obtained (m.p. 114°-115° C. as hydrochloride). 3 g (0.0090 mol) of the above ester (free base) are heated in 70 ml of dimethylamine at 60° C. for 7 hours. The solution is allowed to stand overnight at room temperature, then evaporated and the residue is purified on silica gel (eluant: chloroform/methanol/30% NH4OH; 95/5/0.5) to afford 0.7 g (23%) of [4-(3-chlorobenzyloxy)benzyl]amino-N,N-dimethylacetamide, hydrochloride (m.p. 120°-125° C.). Analogously the following compounds can be obtained, starting from the corresponding ethyl esters:

Workup

  1. customevaporated
  2. customthe residue is purified on silica gel (eluant: chloroform/methanol/30% NH4OH; 95/5/0.5)

Sources & evidence

ORD record
ord-f24dc008fd35401aab60c83ad628bab1
Source dataset
uspto-grants-1993_08
Patent number
US05236957

Reaction notes

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