4-Methylpiperidine → HCID 54444501, compound

HRID 1017553Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:23])[CH2:10][CH:11]([S:19](Cl)(=[O:21])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:23])[CH2:10][CH:11]([S:19]([N:28]1[CH2:29][CH2:30][CH:25]([CH3:24])[CH2:26][CH2:27]1)(=[O:21])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The product from Step H (0.92 g, 2.6 mmol) was taken up in DCM (25 mL) with stirring and cooled to 0° C. TEA (362 μL, 2.6 mmol) and 4-methyl-piperidine (307 μL, 2.6 mmol) were added and the reaction warmed to room temperature and stiired overnight. The reaction was diluted with DCM and washed successively with water, 1 M HCl, water, brine, dried, filtered and concentrated in vacuo to give a yellow oil. This was purified by silica gel column chromatography eluting with hex /EtOAc 8:2 to give the titled compound as a yellow oil (440 mg, 41%). 1H-NMR δ (CDCl3) 7.40-7.18 (10H, m), 5.0 (1H, d, J=12.2 Hz), 4.95 (1H, d, J=12.2 Hz), 3.9 (1H, m), 3.68 (2H, m), 3.42-3.31 (1H, dd, J=4.4, 14.1 Hz), 2.91-2.80 (1H, dd, J=5.9, 17.1 Hz), 2.79-2.62 (3H, m), 2.58-2.47 (1H, dd, J=6.2, 17.1 Hz), 1.69-135 (2H, m), 1.30-1.10 (3H, m) and (3H, d, J=6.2 Hz).

Workup

temperaturethe reaction warmed to room temperature and stiired overnight
washwashed successively with water, 1 M HCl, water, brine
customdried
filtrationfiltered
concentrationconcentrated in vacuo
customto give a yellow oil
customThis was purified by silica gel column chromatography
washeluting with hex /EtOAc 8:2

Sources & evidence

ORD record: ord-d2895ac7cc9c4145b5ec4c25d3d8f650
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479502B1

Reaction notes

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