Dimethylformamide → 4-{4-[3-(2,5-Dimethylpyrrolidin-1-yl)propoxy]phenyl}-tetra-hydropyran-4-carbonitrile

HRID 272901Notes

Reaction equation

HRID 272901 reaction equation
N1(CCC[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.Cl[CH2:25][CH2:26][CH2:27][N:28]1[C@@H:32]([CH3:33])[CH2:31][CH2:30][C@@H:29]1[CH3:34].CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[CH3:34][CH:29]1[CH2:30][CH2:31][CH:32]([CH3:33])[N:28]1[CH2:27][CH2:26][CH2:25][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrileHCID 685770241-(3-Chloro-propyl)-2,5-trans-dimethyl-pyrrolidine

Product 1

HCID 685779264-{4-[3-(2,5-Dimethylpyrrolidin-1-yl)propoxy]phenyl}-tetra-hydropyran-4-carbonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile (318 mg, 1.56 mmol), 1-(3-chloro-propyl)-2,5-trans-dimethyl-pyrrolidine (250 mg, 1.42 mmol), DMF (5 ml) and K2CO3 (785 mg, 5.70 mmol) were reacted together according to general procedure E. The crude was dissolved in ethyl acetate (20 ml), washed with brine (2×10 ml), dried over MgSO4, filtered and concentrated in vacuo to give the title compound (200 mg, 56%) as a light brown solid. 1H NMR (400 MHz, CDCl3), δ 7.37 (d, 2H), 6.93 (d, 2H), 4.13-3.97 (m, 4H), 3.89 (td, 2H), 3.14-2.98 (m, 2H), 2.76 (m, 1H), 2.55 (m, 1H), 2.16-1.88 (m, 8H), 1.46-1.30 (m, 2H), 0.97 (d, 6H).

Workup

  1. washwashed with brine (2×10 ml)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06c3f9326e7d4a59ab341a7904b977df
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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