Potassium Carbonate → 4-[4-(2-Methyl-3-pyrrolidin-1-ylpropoxy)phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 272913Notes

Reaction equation

HRID 272913 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:17][CH:18]([CH3:25])[CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:17][CH:18]([CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:25][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 225682631-(3-Chloro-2-methyl-propyl)-pyrrolidineHCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 598375434-[4-(2-Methyl-3-pyrrolidin-1-ylpropoxy)phenyl]-tetrahydro-pyran-4-carbonitrileYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (790 mg, 3.87 mmol), 1-(3-chloro-2-methyl-propyl)-pyrrolidine (500 mg, 3.10 mmol), DMF (5 ml) and K2CO3 (2.14 g, 15.50 mmol) were reacted together according to general procedure E. The organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml), dried over MgSO4, fitered and concentrated in vacuo at 35° C. to provide the title compound (979 mg, 96%) as a yellow solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.95 (d, 2H), 4.11-4.03 (m, 2H), 4.02 (dd, 1H), 3.89 (td, 2H), 3.77 (dd, 1H), 2.60-2.42 (m, 5H), 2.32 (dd, 1H), 2.22-1.99 (m, 5H), 1.82-1.72 (m, 4H), 1.07 (d, 3H).

Workup

  1. washThe organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationfitered and concentrated in vacuo at 35° C.

Sources & evidence

ORD record
ord-824472b7077a4822b65628bb2103b3ec
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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