Thiomorpholine → HCID 11688302, compound

HRID 1911805Notes

Reaction equation

[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7]CC)=O)[CH2:3][CH2:2]1.[CH3:12][C:13]1[CH:14]=[C:15](Br)[CH:16]=[CH:17][C:18]=1[CH3:19].[NH:21]1[CH2:26][CH2:25][S:24][CH2:23][CH2:22]1>>[CH3:12][C:13]1[CH:14]=[C:15]([N:1]2[CH2:2][CH2:3][CH:4]([C:5]([N:21]3[CH2:26][CH2:25][S:24][CH2:23][CH2:22]3)=[O:7])[CH2:10][CH2:11]2)[CH:16]=[CH:17][C:18]=1[CH3:19]

Participants

Reactant 3

HCID 67164Thiomorpholine

HCID 685044-Bromo-o-xylene

HCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 11688302HCID 11688302, compound

Procedure

The title compound was prepared from commercially available ethyl isonipecotate, 3,4-dimethylbromobenzene as the aryl halide, and thiomorpholine as the secondary amine utilizing general procedures A and B described above. 1H NMR (300 MHz, CDCl3) 1H NMR (CDCl3) δ 7.01 (d, J=7.8 Hz, 1H), 6.76 (d, J=2.3 Hz, 1H), 6.70 (dd, J=2.3, 7.8 Hz, 1H), 3.90 (m, 2H), 3.80 (m, 2H), 2.96 (m, 1H), 2.89 (m, 1H), 2.71-2.50 (m, 7H), 2.23 (s, 3H), 2.18 (s, 3H), 2.04 (dd, J=2.6, 12.2 Hz, 1H), 1.93 (dd, J=3.3, 12.3 Hz, 1H), 1.80 (m, 1H), 1.76 (m, 1H). ESI MS: 319.4 (MH+).

Sources & evidence

ORD record: ord-492d58145e034fbeb0fbc72ad74f98c6
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604190B2

Reaction notes

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