Morpholine → HCID 11681826, compound

HRID 1911802Notes

Reaction equation

HRID 1911802 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7]CC)=O)[CH2:3][CH2:2]1.[Br-].[C:13]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[C:13]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=[C:15]([N:1]2[CH2:2][CH2:3][CH:4]([C:5]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:7])[CH2:10][CH2:11]2)[CH:14]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 70770Ethyl 4-piperidinecarboxylateHCID 22476612HCID 22476612, compound

Product 1

HCID 11681826HCID 11681826, compound

Procedure

The title compound was prepared from commercially available ethyl isonipecotate, m-biphenyl bromide as the aryl halide, and morpholine as the secondary amine utilizing general procedures A and B described above. 1H NMR (300 MHz, CDCl3) δ 7.59-7.30 (m, 6H), 7.14 (t, J=2.0 Hz, 1H), 7.07 (d, J=7.7 Hz, 1H), 6.94 (dd, J=2.0, 7.6 Hz, 1H), 3.85 (m, 1H), 3.80 (m, 1H), 3.63-3.55 (m, 8H), 2.80 (dt, J=2.6, 12.2 Hz, 2H), 2.60 (tt, J=2.8, 11.4 Hz, 1H), 2.07 (dd, J=3.8, 12.8 Hz, 1H), 2.01 (dd, J=4.0, 12.0 Hz, 1H), 1.85 (m, 1H), 1.81 (m, 1H). ESI MS: 351.4 (MH+).

Sources & evidence

ORD record
ord-9f10a4f2cb8d49f1ac860d69aa122466
Source dataset
uspto-grants-2013_12
Patent number
US08604190B2

Reaction notes

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