Piperidine → 2-[4-(4-phenoxyphenylthio)-N-CBZ-piperidin-4-yl]-acetic acid

HRID 1584389Notes

Reaction equation

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

Participants

Reactant 3

HCID 8082Piperidine

HCID 27603544-Phenoxythiophenol

HCID 212243161-Cbz-Piperidin-4-ylidene-acetic acid

Product 1

HCID 212241102-[4-(4-phenoxyphenylthio)-N-CBZ-piperidin-4-yl]-acetic acid

Procedure

4-Phenoxythiophenol (7.4 g, 36.3 mmol), 4-carboxymethylene-N-CBZ-piperidine (10 g, 36.3 mmol) and piperidine (1.8 ml, 36.3 mmol) were stirred overnight at 100-110° C. in a sealed flask. After cooling, the crude reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid, the organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give a yellow solid. The solid was triturated in 1:1 (v/v) ethyl ether/hexane (500 ml) to give 2-[4-(4-phenoxyphenylthio)-N-CBZ-piperidin-4-yl]-acetic acid as a white solid.

Workup

temperatureAfter cooling
customthe crude reaction mixture
customwas partitioned between ethyl acetate and 1N hydrochloric acid
washthe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give a yellow solid
customThe solid was triturated in 1:1 (v/v) ethyl ether/hexane (500 ml)

Sources & evidence

ORD record: ord-71b5d7772a544e08ada83bc8274b1d2f
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932595

Reaction notes

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