Potassium Carbonate → (RS)-2-[4-(3-chloro-benzyloxy)-phenoxy]-N-methyl-propionamide

HRID 853157Notes

Reaction equation

HRID 853157 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH3:12])[C:8]([NH:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:12])[C:8]([NH:10][CH3:11])=[O:9])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 18539804HCID 18539804, compound

Product 1

HCID 69040582(RS)-2-[4-(3-chloro-benzyloxy)-phenoxy]-N-methyl-propionamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In analogy to the procedure described in Example 3b), the alkylation of (RS)-2-(4-hydroxy-phenoxy)-N-methyl-propionamide with 3-chloro-benzylbromide in 2-butanone using potassium carbonate as the base yielded the (RS)-2-[4-(3-chloro-benzyloxy)-phenoxy]-N-methyl-propionamide as a white solid; MS: m/e=320 (M+H)+.

Sources & evidence

ORD record
ord-1a2403e1c66e4f9b8394b34048b0a3a2
Source dataset
uspto-grants-2007_08
Patent number
US07253318B2

Reaction notes

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