Adipic Acid → HCID 68690248, compound

HRID 2242006Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Cl[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl.C(O)CCCCC.[OH-].[Na+].[C:30]([OH:39])(=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36]>C(OC(C)C)(=O)C>[C:30]([OH:39])(=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36].[CH3:13][O:12][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([N:1]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:3]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of 8-amino-6-methoxyquinoline (150.0 g, 0.862 mol) and bis(2-chloroethyl)amine (219 g, 1.23 mol,) in 6 parts (volume of hexanol vs weight of 8-amino-6-methoxyquinoline) of 1-hexanol (900 mL) was heated to 145° C. and stirred for 21 hours. Upon completion, the reaction mixture is cooled 50-60° C., and 507 g of aqueous NaOH solution was added slowly. The reaction mixture was cooled to 25-30° C. and isopropyl acetate (750 mL) was added. The mixture was clarified through a celite pad. The aqueous phase was then split off. The organic solution was treated with a slurry of adipic acid (126 g, 0.862 mol) in isopropyl acetate (250 ml). The resulting mixture was stirred for 16 hours to form 6-methoxy-8-(1-piperazinyl)quinoline adipate salt. The adipate salt was filtered and washed with isopropyl acetate (2×150 ml) and dried by nitrogen flow to give adipate of 6-Methoxy-8-piperazin-1-yl-quinoline (186 g, 55% yield) with ˜97% HPLC area, 88% strength purity in 51% yield.

Workup

temperatureUpon completion, the reaction mixture is cooled 50-60° C.
temperatureThe reaction mixture was cooled to 25-30° C.
customThe aqueous phase was then split off
stirringThe resulting mixture was stirred for 16 hours

Sources & evidence

ORD record: ord-91a0b2b031ec4ba19ac39b2a08322866
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671056B2

Reaction notes

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