Potassium Carbonate → HCID 11703470, compound

HRID 272883Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][NH2:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][N:23]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of {4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (150 mg, 0.47 mmol) and 1-bromo-4-chloroethane (54.2 μL, 0.47 mmol) in anhydrous acetonitrile (5 mL) was added potassium carbonate (65 mg, 0.47 mmol). The mixture was heated to 60° C. overnight then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with DCM:MeOH:NH3 (94:5:1) to give the title compound (40 mg, 23% yield). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 2H), 6.86 (d, 2H), 4.02 (t, 2H), 3.73-3.78 (m, 2H), 3.57-3.53 (m, 2H), 2.65-2.61 (m, 4H), 2.53 (m, 4H), 2.20 (m, 4H), 2.10-1.88 (m, 6H), 1.56 (m, 4H).

Workup

concentrationthen concentrated under reduced pressure
customThe crude product was purified by column chromatography on silica gel eluting with DCM:MeOH:NH3 (94:5:1)

Sources & evidence

ORD record: ord-f2fe244a9e154e7fa96a2609ae15ce98
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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