Potassium Carbonate → HCID 59837508, compound

HRID 272912Notes

Reaction equation

HRID 272912 reaction equation
N1(C[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)CCCC1.ClCC[N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:27]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3([C:22]#[N:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:14][CH:15]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 816691-(2-Chloroethyl)pyrrolidineHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

Product 1

HCID 59837508HCID 59837508, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile (570 mg, 2.82 mmol), 1-(2-chloro-ethyl)-pyrrolidine (300 mg, 2.25 mmol), DMF (5.7 ml) and K2CO3 (1.56 g, 1.13 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. The crude material was subjected to chromatography on silica eluting with 5% MeOH in DCM and gradient to 10% MeOH in DCM to provided the title compound (400 mg, 47%) as an off white solid. 1H NMR (400 MHz, CDCl3), δ 7.38 (d, 2H), 6.95 (d, 2H), 4.13 (t, 2H), 4.10-4.03 (m, 2H), 3.89 (td, 2H), 2.92 (t, 2H), 2.64 (br s, 4H), 2.15-1.99 (m, 4H), 1.88-1.76 (m, 4H).

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-ed6e83431d604f64a891471c076c36aa
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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