Diethylamine → HCID 13769195, compound

HRID 2232563Notes

Reaction equation

HRID 2232563 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][C:20]([OH:22])=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.C1CCCCC1.C(OCC)(=O)C.[CH2:39]([NH:41][CH2:42][CH3:43])[CH3:40]>C(Cl)(Cl)Cl>[CH2:39]([N:41]([CH2:42][CH3:43])[C:20](=[O:22])[CH2:19][CH2:18][O:17][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:16]=1)[CH3:40]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 21283588HCID 21283588, compoundHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 13769195HCID 13769195, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The procedure is as in Example 44, but starting with 3-[(2-phenyl-4-quinolyl)oxy]propanic acid (1.25 g), thionyl chloride (1.25 cc) in chloroform (100 cc) and diethylamine (2.66 cc). After chromatography of the residue on silica gel using the eluant cyclohexane/ethyl acetate (50:50 by volume), N,N-diethyl-3-[(2-phenyl-4-quinolyl)oxy]propanamide (0.43 g), m.p. 94° C., is isolated.

Sources & evidence

ORD record
ord-59239f284ad94e3ab9dcf2804b21f3e8
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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