Dicyclohexylcarbodiimide → S-4-nitrophenyl 3-(4-piperidinopiperidinocarbonyl)propanethioate

HRID 377268

Reaction equation

[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCC(N=C=NC2CCCCC2)CC1.[N+:35]([C:38]1[CH:43]=[CH:42][C:41]([SH:44])=[CH:40][CH:39]=1)([O-:37])=[O:36]>C(Cl)Cl>[N:1]1([CH:7]2[CH2:8][CH2:9][N:10]([C:13]([CH2:15][CH2:16][C:17](=[O:19])[S:44][C:41]3[CH:42]=[CH:43][C:38]([N+:35]([O-:37])=[O:36])=[CH:39][CH:40]=3)=[O:14])[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 4 °C

Procedure

3-(4-Piperidinopiperidinocarbonyl)propionic acid (0.26 g, 0.97 mmol) and DCC (0.25 g, 1.2 mmol) were dissolved in methylene chloride, followed by the addition of 4-nitrothiophenol (0.23 g, 1.2 mmol). The resulting mixture was stirred for 16 hours at 4° C. and then overnight at room temperature. The reaction mixture was filtered. After the filtrate was concentrated, the residue was purified by chromatography on a silica gel column (chloroform-acetone mixed solvent [10:1→5:1], whereby S-4-nitrophenyl 3-(4-piperidinopiperidinocarbonyl)propanethioate (196 mg, 50%) was obtained.

Workup

customovernight
customat room temperature
filtrationThe reaction mixture was filtered
concentrationAfter the filtrate was concentrated
customthe residue was purified by chromatography on a silica gel column (chloroform-acetone mixed solvent [10:1→5:1]

Sources & evidence

ORD record: ord-5ce64b2a2e1e4319b7bcae2833b588f1
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06025385

Linked notes

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