Potassium Carbonate → 4-{4-[3-(2-Methylpyrrolidin-1-yl)-propoxy]-phenyl}tetra-hydropyran-4-carbonitrile

HRID 272902Notes

Reaction equation

HRID 272902 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.Cl[CH2:25]CCN1CCCC1C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:25][CH:2]1[CH2:3][CH2:4][CH2:5][N:1]1[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:22]#[N:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 125732671-(3-Chloro-propyl)-2-methyl-pyrrolidineHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 598374904-{4-[3-(2-Methylpyrrolidin-1-yl)-propoxy]-phenyl}tetra-hydropyran-4-carbonitrileYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile (315 mg, 1.55 mmol), 1-(3-chloro-propyl)-2-methyl-pyrrolidine (400 mg, 2.48 mmol), DMF (6 ml) and K2CO3 (833 mg, 6.03 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 (450 mg, 88%) as an orange oil. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.93 (d, 2H), 4.12-3.99 (m, 4H), 3.89 (td, 2H), 2.35-1.62 (m, 14H), 1.42 (m, 1H), 1.09 (d, 3H).

Workup

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

Sources & evidence

ORD record
ord-5568e774430d482d8811d98de3d8585f
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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