Potassium Carbonate → HCID 59837351, compound

HRID 273057Notes

Reaction equation

HRID 273057 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:18]#[N:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.BrCCCOC1C=CC([C:31]2([C:37]#[N:38])CCOC[CH2:32]2)=CC=1.C([O-])([O-])=O.[K+].[K+].Cl.N1CCC1>C(#N)C>[N:38]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3([C:18]#[N:19])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH2:37][CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12308726Azetidine hydrochlorideHCID 68576421HCID 68576421, compoundHCID 68576473HCID 68576473, compound

Product 1

HCID 59837351HCID 59837351, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-[4-(3-chloro-propoxy)-phenyl]-tetrahydropyran-4-carbonitrile and 4-[4-(3-bromo-propoxy)-phenyl]-tetrahydropyran-4-carbonitrile (7.5 g, 27 mmol), K2CO3 (9.6 g, 70 mmol) and azetidine hydrochloride (4.0 g, 43 mmol) in acetonitrile (80 mL) was heated at 40° C. for 18 hours. The mixture was concentrated in vacuo then partitioned between water (150 mL) and ethyl acetate (150 mL). The organic layer was extracted with 2M HCl solution (2×100 mL) and the combined acid layers basified with 40% potassium hydroxide solution, then extracted with DCM (2×150 mL). The DCM layers were combined, dried over sodium sulphate, filtered and concentrated under reduced pressure to give the title compound (1.1 g, 57%) as a clear, viscous oil. 1H NMR (400 MHz, DMSO) δ 1.80 (quintet, 2H), 2.00-2.14 (m, 6H), 2.58 (t, 2H), 3.20 (t, 4H), 3.88 (m, 2H), 4.00-4.11 (m, 4H), 6.90 (d, 2H), 7.38 (d, 2H). LRMS (APCI+) m/z 301 (MH)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthen partitioned between water (150 mL) and ethyl acetate (150 mL)
  3. extractionThe organic layer was extracted with 2M HCl solution (2×100 mL)
  4. extractionextracted with DCM (2×150 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7ca4d9128234df6ab66195616eacf40
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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