2-Bromotoluene → HCID 11695190, compound

HRID 1911800Notes

Reaction equation

HRID 1911800 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7]CC)=O)[CH2:3][CH2:2]1.[C:12]1([CH3:19])[C:13](Br)=[CH:14][CH:15]=[CH:16][CH:17]=1.[NH:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1>>[C:12]1([CH3:19])[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[N:1]1[CH2:2][CH2:3][CH:4]([C:5]([N:20]2[CH2:25][CH2:24][S:23][CH2:22][CH2:21]2)=[O:7])[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 72362-BromotolueneHCID 67164ThiomorpholineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 11695190HCID 11695190, compound

Procedure

The title compound was prepared from commercially available ethyl isonipecotate, o-tolyl bromide as the aryl halide, and thiomorpholine as the secondary amine utilizing general procedures A and B described above. 1H NMR (300 MHz, CDCl3) δ 7.19-7.13 (m, 2H), 7.00-6.95 (m, 2H), 3.95 (m, 2H), 3.82 (m, 2H), 3.21 (m, 1H), 3.17 (m, 1H), 2.71-2.54 (m, 7H), 2.30 (s, 3H), 2.09 (dd, J=3.6, 13.1 Hz, 1H), 2.00 (dd, J=3.6, 12.0 Hz, 1H), 1.79 (m, 1H), 1.75 (m, 1H). ESI MS: 305.3 (MH+).

Sources & evidence

ORD record
ord-80b5a2bb146e446a8ecbbc7efc45c118
Source dataset
uspto-grants-2013_12
Patent number
US08604190B2

Reaction notes

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