Chloroform → HCID 23294371, compound

HRID 1955196Notes

Reaction equation

HRID 1955196 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)[CH2:5][CH2:4]1)#N.COC1C=CC(OCC[N:29]2[CH2:37][CH2:36][CH:32](C(N)=O)[CH2:31][CH2:30]2)=CC=1.C(Cl)(Cl)[Cl:41]>>[ClH:41].[ClH:41].[OH:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][N:6]2[CH2:5][CH2:4][CH:3]([CH2:1][C:30]3[CH:31]=[CH:32][CH:36]=[CH:37][N:29]=3)[CH2:8][CH2:7]2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 9442922HCID 9442922, compoundHCID 23294429HCID 23294429, compound

Product 1

HCID 23294371HCID 23294371, compound

Conditions

Temperature
25 °C

Procedure

4-Cyano-1-(2-(4-methoxyphenoxy)ethyl)piperidine. To a stirred suspension of 1-(2-(4-methoxyphenoxy)ethyl)isonipecotamide (10.0 g, 35.9 mmol) in CHCl3 (80 mL) neat SOCl2 (30 mL) was added drop wise over 5 min. The resulting suspension was heated at reflux with stirring under N2 for 1 h. The reaction was allowed to cool to 25° C. and the volatile portion was removed to give a yellow syrup. The syrup was partitioned between CHCl3 and H2O (200 mL) each. The stirred yellow mixture was made basic by the addition of concd NH4OH (50 mL) to give a pink mixture. The layers were separated and the aqueous portion was extracted with CHCl3 (2×50 mL). The combined organic portion was washed with 10% NH4OH, H2O and brine (200 mL each), was filtered through cotton and the solvent was removed to give a red oil that partially solidified upon standing. The product was purified on silica gel (3.5×25 cm) with CHCl3 then 2% EtOH/98% CHCl3 elution to yield the title compound as an amber oil that solidified to a beige solid upon standing (6.8 g, 73%): mp 49-51° C.; 1H NMR (CDCl3) 1.78-2.03 (m, 4H), 2.40-2.54 (m, 2H), 2.58-2.84 (m, 5H), 3.76 (s, 3H), 4.03 (t, J=5.7 Hz, 2H), 6.83 (s, 4H).

Workup

  1. additionwas added drop wise over 5 min
  2. temperatureThe resulting suspension was heated
  3. temperatureat reflux
  4. customthe volatile portion was removed
  5. customto give a yellow syrup
  6. customThe syrup was partitioned between CHCl3 and H2O (200 mL) each
  7. additionThe stirred yellow mixture was made basic by the addition of concd NH4OH (50 mL)
  8. customto give a pink mixture
  9. customThe layers were separated
  10. extractionthe aqueous portion was extracted with CHCl3 (2×50 mL)
  11. washThe combined organic portion was washed with 10% NH4OH, H2O and brine (200 mL each)
  12. filtrationwas filtered through cotton
  13. customthe solvent was removed
  14. customto give a red oil that
  15. customThe product was purified on silica gel (3.5×25 cm) with CHCl3
  16. wash2% EtOH/98% CHCl3 elution

Sources & evidence

ORD record
ord-14244053aca845349e1634880b4af557
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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