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Dimethylformamide → 5-Ethyl-3-(piperidine-1-carbonyl)-thiophene-2-carbonitrile

HRID 1809083
Notes
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Reaction equation

HRID 1809083 reaction equation
Br[C:2]1[S:3][C:4]([CH2:15][CH3:16])=[CH:5][C:6]=1[C:7]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:8].[CH3:17][N:18](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:15]([C:4]1[S:3][C:2]([C:17]#[N:18])=[C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])[CH:5]=1)[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 42643628(2-Bromo-5-ethyl-thiophen-3-yl)-piperidin-1-yl-methanone

Product 1

HCID 426438755-Ethyl-3-(piperidine-1-carbonyl)-thiophene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladium
Catalyst

Conditions

Temperature
100 °C

Procedure

(2-Bromo-5-ethyl-thiophen-3-yl)-piperidin-1-yl-methanone (0.1 g, 0.33 mmol) was dissolved in DMF (3 mL). Zinc cyanide (0.34 mmol) and tetrakis-(triphenylphosphine) palladium (0) (0.017 mmol) were added and the reaction mixture heated at 100° C. for 4 hours. The mixture was cooled to ambient temperature and the reaction quenched with a mixture of 5% aqueous sodium thiosulphate and saturated aqueous potassium carbonate (1:1, 5 mL) and extracted with diethyl ether. The organic solution was dried over magnesium sulphate, filtered and the solvent removed. The product was purified by HPLC, eluting with 20%-95% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum and freeze-dried to give the title compound (0.26 mg). LCMS m/z 249.14 [M+H]+ RT=9.75 min (Analytical Method 1). 1H NMR (400 MHz, CHCl3-d): δ 6.85 (t, 1H), 3.70 (m, 2H), 3.4 (m, 2H), 2.9 (m, 2H), 1.7 (m, 4H), 1.6 (s, 2H), 1.3 (t, 3H).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe reaction quenched with a mixture of 5% aqueous sodium thiosulphate and saturated aqueous potassium carbonate (1:1, 5 mL)
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic solution was dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe product was purified by HPLC
  8. washeluting with 20%-95% acetonitrile in water (0.1% formic acid) over 30 minutes
  9. additionThe fractions containing the desired product
  10. concentrationwere concentrated under vacuum
  11. customfreeze-dried

Sources & evidence

ORD record
ord-5a7370f56d1943b0a68b47d00c4f473c
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362008B2

Reaction notes

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