Potassium Carbonate → 4-[3-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-carbonitrile

HRID 272900

Reaction equation

HRID 272900 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:17][CH2:18][CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:20]1([CH2:19][CH2:18][CH2:17][O:1][C:2]2[CH:3]=[C:4]([C:8]3([C:14]#[N:15])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[CH:5]=[CH:6][CH:7]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112871604-Cyano-4-(3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyranHCID 113210281-(3-Chloropropyl)-pyrrolidine

Product 1

HCID 598374824-[3-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-carbonitrileYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-Hydroxy-phenyl)-tetrahydro-2H-pyran-4-carbonitrile (1.03 g, 5.10 mmol), 1-(3-chloro-propyl)-pyrrolidine (600 mg, 4.08 mmol), DMF (6.8 ml) and K2CO3 (2.82 g, 20.4 mmol) were reacted together according to general procedure E. The organic phase was washed with 2M NaOH (3×50 ml), brine (3×50 ml), dried over MgSO4, fitered and concentrated in vacuo at 35° C. The crude mixture was slurried in TBME:heptane (1:20, 10 ml). The solid was filtered, washed with heptane (10 ml) and dried on the filter for 2 hours to give the title compound (0.4 g, 31%). 1H NMR (400 MHz, CDCl3) δ 7.32 (t, 1H), 7.07-6.99 (m, 2H), 6.87 (dd, 1H), 4.11-4.04 (m, 2H), 4.05 (t, 2H), 3.90 (td, 2H), 2.63 (t, 2H), 2.57-2.49 (m, 4H), 2.18-1.97 (m, 6H), 1.84-1.75 (m, 4H).

Workup

  1. washThe organic phase was washed with 2M NaOH (3×50 ml), brine (3×50 ml)
  2. dry with materialdried over MgSO4
  3. concentrationfitered and concentrated in vacuo at 35° C
  4. filtrationThe solid was filtered
  5. washwashed with heptane (10 ml)
  6. customdried on the
  7. filtrationfilter for 2 hours

Sources & evidence

ORD record
ord-974f952d1fee4b1e95f6200d1092d00b
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Linked notes

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