Piperidine → HCID 54721665, compound

HRID 481897Notes

Reaction equation

HRID 481897 reaction equation
Br[C:2]1[C:3](=[O:23])[O:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C:7]=1[OH:8].[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[C:27]([CH:32]([CH3:34])[CH3:33])[CH:26]=1.N1CCCCC1>ClCCl>[OH:8][C:7]1[CH2:6][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:4][C:3](=[O:23])[C:2]=1[S:31][C:28]1[CH:29]=[CH:30][C:25]([CH3:24])=[CH:26][C:27]=1[CH:32]([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 21222409HCID 21222409, compoundHCID 547216393-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 54721665HCID 54721665, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 2.0 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (prepared in example BBB), 2.1 mmol of 4-methyl-2-isopropylbenzenethiol, and 2.1 mmol of piperidine in 30 mL of dichloromethane. The product was chromatographed on silica gel, eluting first with chloroform and then with 5% methanol in chloroform (m.p. 75°-76° C.). 1H NMR (DMSO-d6) δ1.15 (m, 6H), 2.16 (s, 3H), 2.19-2.36 (m, 3H), 2.62 (m, 1H), 3.21 (m, 1H), 3.44 (q, 2H), 5.82 (d, 1H), 6.40 (dd, 1H), 6.95 (d, 1H), 7.10-7.18 (m, 3H), 7.25 (m, 2H), 7.44 (m, 5H).

Workup

  1. customThe product was chromatographed on silica gel
  2. washeluting first with chloroform

Sources & evidence

ORD record
ord-4fc926827a62457c9178ad8057fdeadd
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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