Potassium Carbonate → 4-[4-(3-Thiomorpholin-4-ylpropoxy)phenyl]tetrahydropyran-4-carbonitrile

HRID 272903Notes

Reaction equation

HRID 272903 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([C:22]#[N: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.ClCCCN1CC[S:31]CC1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:1]1([CH2:6][CH2:7][CH2:8][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)[CH2:5][CH2:4][S:31][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 230916864-(3-Chloro-propyl)-thiomorpholineHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 598374964-[4-(3-Thiomorpholin-4-ylpropoxy)phenyl]tetrahydropyran-4-carbonitrileYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile (750 mg, 3.69 mmol), 4-(3-chloro-propyl)-thiomorpholine (1.06 g, 5.91 mmol), DMF (15 ml) and K2CO3 (2.05 g, 14.83 mmol) were reacted together according to general procedure E. Purification by chromatography on silica, eluant DCM:MeOH:NH3 (96:3:1) provided the title compound (365 mg, 29%) as an off white solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.93 (d, 2H), 4.12-4.04 (m, 2H), 4.01 (t, 2H), 3.89 (td, 2H), 2.77-2.64 (m, 8H), 2.54 (t, 2H), 2.16-1.99 (m, 4H), 1.95 (p, 2H).

Workup

  1. customPurification by chromatography on silica, eluant DCM:MeOH:NH3 (96:3:1)

Sources & evidence

ORD record
ord-c0053c10146647d498ea73bc7a5f6c5e
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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