Piperidine → HCID 54721731, compound

HRID 357895Notes

Reaction equation

HRID 357895 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(CCC2C=CC=CC=2)[O:5][C:4](=[O:22])[CH:3]=1.C1C(=O)N(Br)C(=O)C1.[CH:31]([N:34]1[CH2:39][CH2:38][CH2:37][NH:36][C:35]1=[S:40])([CH3:33])[CH3:32].N1CCCCC1>C(Cl)Cl.C(O)(C)(C)C>[OH:1][C:2]1[CH2:7][CH:6]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:5][C:4](=[O:22])[C:3]=1[S:40][C:35]1[N:34]([CH:31]([CH3:33])[CH3:32])[CH2:39][CH2:38][CH2:37][N:36]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 67184N-bromobutanimideHCID 124104181-(Propan-2-yl)tetrahydropyrimidine-2(1H)-thioneHCID 546823015,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 54721731HCID 54721731, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6386tert-ButanolSolvent

Procedure

The title compound was prepared as described in example 41 using the following: 5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (0.250 g, 0.850 mmol), t-butanol (3.5 mL), n-bromosuccinimide (0.151 g, 0.85 mmol), CH2Cl2 (6.0 mL), 1-isopropyltetrahydropyrimidine-2-thione (0.270 g, 1.70 mmol, prepared by the method described by A. F. McKay et al., J. Am. Chem. Soc., 78: 1618 (1956)), piperidine (0.084 mL, 0.85 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 1/1 CH2Cl2 /ethyl acetate to 2/14/1 ethyl acetate/CH2Cl2 /methanol) to provide a solid which was redissolved in CH2Cl2, filtered through a fiberglass filter, and the solvent removed in vacuo to provide the title compound (0.356 g, m.p. 103°-105° C). 1H NMR (400 MHz, DMSO-d6) δ 7.440-7.371 (m, 4 H), 7.296 (t, 1 H, J=7 Hz), 7.233 (t, 2 H, J=7 Hz), 7.139 (t, 1 H, J=7 Hz), 7.077 (d, 2 H, J=7 Hz), 6.515 (bs, 1 H), 4.365-4.300 (m, 1 H), 3.335-3.308 (m, 2 H), 3.024 -2.924 (m, 4 H), 2.624-2.548 (m, 1 H), 2.341-2.265 (m, 1 H), 2.156-2.061 (m, 2 H), 1.763-1.737 (m, 2 H), 1.201-1.180 (m, 6 H).

Workup

  1. customThe title compound was prepared
  2. customprepared by the method
  3. customPurification
  4. customto provide a solid which
  5. filtrationfiltered through a fiberglass
  6. filtrationfilter
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d41e7cc4d8684f85a11681e642af77e1
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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