Potassium Carbonate → HCID 59837456, compound

HRID 272906Notes

Reaction equation

HRID 272906 reaction equation
N1(CCC[O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)CCCC1.Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH2:35][OH:36])[CH2:30][CH2:29]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:36][CH2:35][CH2:34][CH:31]1[CH2:32][CH2:33][N:28]([CH2:27][CH2:26][CH2:25][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 404243272-[1-(3-Chloropropyl)piperidin-4-yl]ethan-1-olHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 59837456HCID 59837456, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile (185 mg, 0.91 mmol), 2-[1-(3-chloro-propyl)-piperidin-4-yl]-ethanol (300 mg, 1.46 mmol), DMF (4 ml) and K2CO3 (497 mg, 3.60 mmol) were reacted together according to general procedure E. Purification by chromatography on silica, eluant DCM:MeOH:NH3 (92:6:2) provided the title compound (220 mg, 65%) as a pale pink solid. 1H NMR (400 MHz, CDCl3) δ 7.37 (d, 2H), 6.93 (d, 2H), 4.11-4.04 (m, 2H), 4.01 (t, 2H), 3.89 (td, 2H), 3.70 (t, 2H), 2.97-2.87 (m, 2H), 2.48 (t, 2H), 2.15-1.88 (m, 8H), 1.77-1.57 (m, 3H), 1.57-1.38 (m, 3H), 1.35-1.21 (m, 2H).

Workup

  1. customPurification by chromatography on silica, eluant DCM:MeOH:NH3 (92:6:2)

Sources & evidence

ORD record
ord-0cd3a120e0d64814a54e968d7e93926a
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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