Potassium Carbonate → HCID 18782783, compound

HRID 1420701Notes

Reaction equation

I[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[ClH:18].[CH:16]1[C:17]2[N:5]([CH2:4][CH2:3][CH2:2][N:28]3[CH2:27][CH2:26][C:25]([C:22]4[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=4)([OH:31])[CH2:30][CH2:29]3)[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Compound 3 (2.58 g, 0.0056 mol) was dissolved in dry DMF (80 mL), 4-(4-chlorophenyl)piperidin-4-ol (1.0 g, 0.0047 mol) and K2CO3 (0.57 g, 0.0056 mol) were added. The resulting mixture was stirred at 50-60° C for 12 h and at room temperature for 48 h. The reaction mixture was concentrated to dryness in vacuo and CH2Cl2 (100 mL) was added. The organic phase was washed with 5% NaHCO3 (aq) (100 mL), brine (50 mL), dried (MgSO4), filtered and the solvent evaporated in vacuo, to give 4.8 g of an oil. The residual oil was purified on a silica gel column (Eluent: ethyl acetate/n-heptane (1:1)). The product was acidified with 2M HCl(g) in diethylether, giving the title compound 1.6 g (75%). M.p. 194.5-195.5° C.

Workup

concentrationThe reaction mixture was concentrated to dryness in vacuo and CH2Cl2 (100 mL)
additionwas added
washThe organic phase was washed with 5% NaHCO3 (aq) (100 mL), brine (50 mL)
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-6e9e308a06ee41ffb5ff2a7bcbed1669
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071932

Reaction notes

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