Piperidine → HCID 54681350, compound

HRID 613112Notes

Reaction equation

HRID 613112 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:14])[CH:3]=1.[CH:15](=O)[CH2:16][CH:17]([CH3:19])[CH3:18].[CH:21]1([SH:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.N1CCCCC1.[K+].[Br-]>C(O)C.C(O)(=O)C>[CH:21]1([S:27][CH:15]([C:3]2[C:4](=[O:14])[O:5][C:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:7][C:2]=2[OH:1])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

8

Reactant 5

HCID 8082PiperidineHCID 115523-MethylbutanalHCID 15290CyclohexanethiolHCID 253877Potassium BromideHCID 546956304-Hydroxy-6-phenyl-2H-pyran-2-one

Product 1

HCID 54681350HCID 54681350, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The title compound was prepared by Method C using 4-hydroxy-6 -phenyl-2H-pyran-2-one (1.5 g, 7.98 mmol), isovaleraldehyde (076 g, 8.78 mmol), cyclohexylmercaptan (2.04 g, 17.56 mmol), piperidine, (1.0 mL), acetic acid (1.0 mL) and ethanol (20 mL).m.p. 210-212° C.; 1H NMR (400 MHz, DMSO-d6) δ0.89 (t, 6 H), 1.36 (m, 6 H), 1.44 (m, 1 H), 1.56 (m, 2 H), 1.69 (m, 2 H), 1.81 (m, 1 H), 2.08 (m, 2 H), 2.61 (brm, 1 H), 4.22 (m, 1 H), 6.67 (s, 1 H), 7.53 (m, 3 H), 7.78 (m, 2 H); IR (KBr) 3106, 2928, 2851, 1659, 1568, 1404, 1125, 766, 569 cm-1 ; MS (CI) m/e 259 (50), 257 (49), 201 (46), 189 (16), 147 (8), 105 (28), 83 (100).

Sources & evidence

ORD record
ord-51199975a8c74b22b15d41de85d42800
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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