Potassium Carbonate → HCID 87571300, compound

HRID 1711126Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][O:14][C:13]2=[S:23])[CH2:8][CH2:7]1)[CH3:5].C([O-])([O-])=O.[K+].[K+]>>[NH2:1][CH2:2][CH2:3][C@@H:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][O:14][C:13]2=[S:23])[CH2:8][CH2:7]1)[CH3:5]

Participants

Reactant 2

HCID 11430Potassium Carbonate

HCID 59458250HCID 59458250, compound2×

Product 1

HCID 87571300HCID 87571300, compoundYield 42%

Procedure

Using general procedure C the substrate (5.0 g, 0.012 mol) gave the desired amine. Due to the high water solubility of the compound, the mixture was neutralized with solid K2CO3 and the product was purified by column chromatography to afford (R,S)-3-[1-(3-amino-1-methyl-propyl)-piperidine-4-yl]-4-phenyl-oxazolidine-2-thione (1.6 g, 42%). 1H NMR (CDCl3) δ 0.90 (d, 3H), 0.90-1.0 (m, 1H), 1.31-1.91 (m, 8H), 2.03-2.05 (m, 1H), 2.61-2.75 (m, 6H), 4.32-4.36 (m, 2H), 4.94-4.98 (m, 1H), 5.29 (d, 1H), 7.25-7.42 (m, 5H).

Workup

customthe product was purified by column chromatography

Sources & evidence

ORD record: ord-c4ed0525c8bb44809a6fd71c7ec4ff73
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790747B2

Reaction notes

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