Hydrochloric Acid → HCID 19762431, compound

HRID 248914Notes

Reaction equation

HRID 248914 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[CH:5]=1.[OH-].[Na+].Cl>CO>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([CH2:11][O:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:22])=[O:2])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53724944HCID 53724944, compound

Product 1

HCID 19762431HCID 19762431, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-Quinolinylmethoxy)benzoic acid methyl ester (10.25 g, 35 mmol) and 2.5N NaOH (aq) (70 ml, 175 mmol) were refluxed for 2 hours in MeOH (300 mL). Neutralization with conc. HCl (14.5 mL, 175 mmol) and filtration afforded 9.5 g (34 mmol, 97%) of air-dried 3-(4-quinolinylmethoxy)benzoic acid as a white solid. The free acid (9.0 g, 32 mmol) was refluxed in excess thionyl chloride (50 mL, neat) for 10 minutes. Dichloroethane and ether were added and the resulting precipitate filtered to afford 3-(4-quinolinylmethoxy)benzoyl chloride hydrochloride as a cream colored solid. The acid chloride (3.34 g, 10 mmol), resuspended in methylene chloride, was treated with 4-amino-1-benzylpiperidine (3.80 g, 20 mmol) and, after 0.5 hours, extracted with 1N NaOH (aq) and water. Evaporation of the organic phase, crystallization of the residue from methylene chloride-ether-hexane, and purification by flash column chromatography on silica gel afforded, after recrystallization from acetonitrile, 3.1 g (6.9 mmol, 69% yield) of the product as a pale yellow solid, m.p. 160°-163° C.

Sources & evidence

ORD record
ord-9e6c9f1408484baa89361b6aaa88a59d
Source dataset
uspto-grants-1993_05
Patent number
US05212182

Reaction notes

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