Morpholine → HCID 58089855, compound

HRID 251611Notes

Reaction equation

Cl[C:2]([C:9]1[C:10]([O:25][CH2:26][CH3:27])=[CH:11][C:12]([C:15]2[C:20]([CH2:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:23][CH3:24])=[N:13][CH:14]=1)([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][CH3:5].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>O>[CH2:23]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH2:21][CH3:22])[C:15]=1[C:12]1[N:13]=[CH:14][C:9]([C:2]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][CH3:5])=[C:10]([O:25][CH2:26][CH3:27])[CH:11]=1)[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(1-chloro-1-propyl-butyl)-2-(2,6-diethyl-phenyl)-4-ethoxy-pyridine (prepared using a synthetic method similar to that given in Example 10) (20 mg, 0.052 mmol) and morpholine (0.5 mL) is heated to 80° C. for 2 hours. Water (1 mL) is added and the aqueous solution is extracted with ethyl acetate (2×2 mL). The combined organic layers are dried and concentrated in vacuo. The crude product is purified with PTLC (hexanes/ethyl acetate 4:1) to give 4-{1-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-1-propyl-butyl}-morpholine. 1H NMR: (CDCl3) 8.66 (s, 1H), 7.26 (m, 1H), 7.12 (d, 2H), 6.71 (S, 1H), 4.02 (q, 2H), 3.70 (m, 4H), 2.64 (m, 4H), 2.34 (m, 4H), 1.88 (m, 4H), 1.43 (t, 3H), 1.07 (m, 4H), 1.02 (t, 6H), 0.84 (t, 6H).

Workup

customprepared
extractionthe aqueous solution is extracted with ethyl acetate (2×2 mL)
customThe combined organic layers are dried
concentrationconcentrated in vacuo
customThe crude product is purified with PTLC (hexanes/ethyl acetate 4:1)

Sources & evidence

ORD record: ord-84bf1674cb9445338a32cca9ae5452cc
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863454B2

Reaction notes

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