3-Bromo-o-xylene → HCID 11645379, compound

HRID 1911801Notes

Reaction equation

HRID 1911801 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[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1Br.[OH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>>[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[N:1]1[CH2:2][CH2:3][CH:4]([C:5]([N:25]2[CH2:26][CH2:27][CH:22]([OH:21])[CH2:23][CH2:24]2)=[O:7])[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 684723-Bromo-o-xyleneHCID 70770Ethyl 4-piperidinecarboxylateHCID 79341Piperidin-4-ol

Product 1

HCID 11645379HCID 11645379, compound

Procedure

The title compound was prepared from commercially available ethyl isonipecotate, 2,3-dimethylbromobenzene as the aryl halide, and 4-hydroxypiperidine as the secondary amine utilizing general procedures A and B described above. 1H NMR (300 MHz, CDCl3) δ 7.06 (d, J=7.7 Hz, 1H), 6.90 (d, J=7.7 Hz, 2H), 4.12 (m, 1H), 3.96 (m, 1H), 3.83 (m, 1H), 3.33-3.13 (m, 4H), 2.70-2.61 (m, 3H), 2.27 (s, 3H), 2.22 (s, 3H), 2.12-1.43 (m, 8 H). ESI MS: 317.4 (MH+).

Sources & evidence

ORD record
ord-ac1530493cb744a3a46a05adba54f853
Source dataset
uspto-grants-2013_12
Patent number
US08604190B2

Reaction notes

Loading…