Ethanol → HCID 68968162, compound

HRID 268722Notes

Reaction equation

HRID 268722 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:7]=[CH:6]C=1C#N.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23]>>[ClH:1].[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][C:23]=1[C:22]([OH:20])=[O:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 17986267HCID 17986267, compound

Product 1

HCID 68968162HCID 68968162, compound

Conditions

Temperature
120 °C

Procedure

2-Chloro-4-(3-piperidin-1-ylpropoxy)benzonitrile (D26) (6.29 g) with aqueous 1M sodium hydroxide (45.2 ml) in ethanol (60 ml) was heated at reflux for 72 h. The reaction mixture was then evaporated to remove ethanol and the aqueous solution treated with excess conc. hydrochloric acid and heated at 120° C. for 2 h. The reaction mixture was then cooled to 5° C. and filtered. The filter cake was washed with a small volume of water and then acetone followed by drying at 65° C. under high vacuum overnight to give the title compound (D27) as a pale brown powder (6.48 g). MS electrospray (+ion) 298/230 (MH+). 1H NMR δ (DMSO-d6): 13.05 (1H, s), 10.85 (1H, s), 7.89 (1H, d, J=8.7 Hz), 7.10 (1H, s), 7.02 (1H, d, J=8.7 Hz), 4.16 (2H, t, J=6.0 Hz), 3.40 (2H, m), 3.13 (2H, m), 2.88 (2H, m), 2.23 (2H, m), 1.94-1.35 (6H, m).

Workup

  1. temperatureat reflux for 72 h
  2. customThe reaction mixture was then evaporated
  3. customto remove ethanol
  4. additionthe aqueous solution treated with excess conc. hydrochloric acid
  5. temperatureThe reaction mixture was then cooled to 5° C.
  6. filtrationfiltered
  7. washThe filter cake was washed with a small volume of water
  8. customby drying at 65° C. under high vacuum overnight

Sources & evidence

ORD record
ord-efd6204974084c92bacc16c6c173b2f6
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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