Hydrochloric Acid → 3-[5-(1-Quinolin-2-ylmethyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile

HRID 1791366Notes

Reaction equation

HRID 1791366 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[N:8]=1.Cl.Cl[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.C(N(C(C)C)CC)(C)C.Cl>CN(C=O)C.CCOCC.O>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[CH2:22][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[N:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 103549563-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile

Product 1

HCID 100692683-[5-(1-Quinolin-2-ylmethyl-piperidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

3-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (50.8 mg, 0.2 mmol) was mixed with 2-(chloromethyl)quinoline monohydrochloride (47.1 mg, 0.22 mmol) and diisopropylethylamine (129.3 mg, 1.0 mmol) in DMF (2 mL) at 80° C. for 20 h. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water and brine, dried with sodium sulfate, purified by column chromatography with 5˜10% ethyl acetate in hexanes to give a colorless sticky oil. This sticky oil was mixed with 1 M HCl in ether (0.4 mL) and triturated with ethyl acetate to give an off-white solid, 45 mg (48%). 1H NMR (CDCl3+DMSO-d6), δ(ppm): 8.92 (d, 1H), 8.70 (d, 1H), 8.16 (m, 3H), 8.07 (d, 1H), 8.00 (t, 1H), 7.84 (m, 2H), 7.63 (m, 1H), 4.64 (m, 3H), 3.30 (m, 1H), 2.86(m, 1H), 2.04–2.38 (m, 2H), 1.57–1.90 (m, 4H).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. custompurified by column chromatography with 5˜10% ethyl acetate in hexanes
  5. customto give a colorless sticky oil
  6. customtriturated with ethyl acetate
  7. customto give an off-white solid, 45 mg (48%)

Sources & evidence

ORD record
ord-6ab5f886a86e44dfae5f95c005cece48
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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