[Cl-].[C:2]([C:5]1[CH:17]=[CH:16][C:8]([CH2:9][NH+:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)(O)=[O:3].CN(C=O)C.S(Cl)([Cl:25])=O>C1(C)C=CC=CC=1>[N:10]1([CH2:9][C:8]2[CH:16]=[CH:17][C:5]([C:2]([Cl:25])=[O:3])=[CH:6][CH:7]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1A 200 mL round-bottom flask fitted with a reflux condenser was charged with 4-(4-carboxy-benzyl)-morpholin-4-ium chloride (10.0 g, 0.039 mol, 1.0 eq), toluene (50 mL), DMF (0.3 mL, 0.0039 mol, 0.1 eq), and thionyl chloride (7.1 mL, 0.097 mol, 2.5 eq) under a nitrogen atmosphere. The reaction mixture was heated to 70° C. for 6 h and then cooled to 0° C. The resulting mixture was filtered and the solid washed with pentane to yield 4-morpholin-4-ylmethyl-benzoyl chloride, which was used in the next step without further purification.
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