Morpholine → 4-(4-(Benzyloxy)-6-chloropyridin-2-yl)morpholine

HRID 594093

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[C:11]([Cl:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CN1C(=O)CCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Cl:16])[N:12]=[C:13]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-(benzyloxy)-2,6-dichloropyridine (1.0 equiv.) and morpholine (1.2 equiv.) in NMP (2 M) were heated to 130° C. for 1 h in the microwave. The reaction mixture was partitioned between water and EtOAc. The organic phase was washed with brine and dried over sodium sulfate. The solution was concentrated and dried under vacuo to give crude 4-(4-(benzyloxy)-6-chloropyridin-2-yl)morpholine and was used in the next step without further purification. LCMS (m/z) (M+H)=305.0, Rt=1.10 min.

Workup

customThe reaction mixture was partitioned between water and EtOAc
washThe organic phase was washed with brine
dry with materialdried over sodium sulfate
concentrationThe solution was concentrated
customdried under vacuo

Sources & evidence

ORD record: ord-c2eedfd2ac7642efb0746d80526589d0
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242969B2

Linked notes

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