Cyclopentanone → Cyclohexanone, 2-[(2-oxocyclopentyl)methyl]-

HRID 437089

Reaction equation

HRID 437089 reaction equation
C[N:2](CC1CCCCC1=O)C.C1(=O)CCCC1.[O:18]=[C:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][C:26]1=[O:31]>>[O:18]=[C:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][C:26]1=[O:31].[CH2:21]1[C:20]2[C:19](=[N:2][C:26]3[CH2:27][CH2:28][CH2:29][CH2:30][C:25]=3[CH:24]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 858382-((Dimethylamino)methyl)cyclohexanoneHCID 4738124Cyclohexanone, 2-[(2-oxocyclopentyl)methyl]-

Product 2

HCID 4738124Cyclohexanone, 2-[(2-oxocyclopentyl)methyl]-Yield 80%HCID 98128865,6,7,8-Tetrahydro-2,3-dihydro-1H-cyclopenta [b]quinoline

Procedure

2-(oxo-cyclopentyl)methyl cyclohexanone is prepared from 2-(dimethylaminomethyl)-cyclohexanone and cyclopentanone according to the method described in Ann.Chim.,1963, 53 (6), 819 and is isolated as a colourless oil in 80% yield b.p. 92°/0.05 mm. 5,6,7,8-Tetrahydro-2,3-dihydro-1H-cyclopenta [b]quinoline is prepared from 2-(2-oxocylopentyl)methylcyclohexanone according to the method described in Ann.Chim., 1963, 53,(6), 819 and is isolated in 65% yield as a colourless oil b.p. 80°/0.05 mm. The hydrochloride is prepared for characterisation by treating an ethereal solution of the base with ethereal HC1 and is isolated as the hemi-hydrate as colourless needles from ethanol-ester m.p. 104° C(Found: C65.7; H,7.8; N,6.6 C12H16N.HC1.1/2H2O requires: C,65.8; H,7.8; N,6.4%. 5,6,7,8-tetrahydro-2,3-dihydro-1H-cyclopenta[b]-quinoline is converted to methyl 5,6,7,8-tetrahydro-2,3-dihydro-1H-cyclopenta[b]quinoline-5-carboxylate following the method described in Example 19 and this is converted to 5,6,7,8-tetrahydro-2,3-dihydro-1H-cyclopenta[b]-quinoline-5-carboxamide following the method described in Example 22. The amide is converted to the title compound, following the procedure of Example 23, and is recrystallised from isopropanol, dissolved in ether and treated with an excess of ethereal HC1. The resultant solid is recrystallised from ethanol-ether to give the hydrochloride of the title compound as the monohydrate m.p. 118° C. )Found: C,54.6; H,6.3; N,10.0 C13H16N2S.HCl H2O requires: C,54.4; H,6.6; N,9.8%).

Workup

  1. customis isolated as a colourless oil in 80% yield b.p. 92°/0.05 mm

Sources & evidence

ORD record
ord-ba420a246c674c8fb01da79c7c2b9287
Source dataset
uspto-grants-1977_06
Patent number
US04029668

Linked notes

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