Hydrochloric Acid → HCID 57831207, compound

HRID 1642023Notes

Reaction equation

HRID 1642023 reaction equation
[OH:1][C:2]1([C:21]#N)[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]=[N:17][N:18]([CH3:20])[N:19]=3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.Cl.[OH-:24].[Na+].[CH2:26]([OH:28])[CH3:27]>>[OH:1][C:2]1([C:21]([O:28][CH2:26][CH3:27])=[O:24])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]=[N:17][N:18]([CH3:20])[N:19]=3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 57831205HCID 57831205, compound

Product 1

HCID 57831207HCID 57831207, compound

Conditions

Temperature
55 °C

Procedure

A solution of 9.6 grams (0.032 mole) of 4-hydroxy-1-{[4-(2-methyl(1,2,3,4-tetrazol-5-yl))phenyl]methyl}piperidine-4-carbonitrile in 200 mL of ethanol was saturated with gaseous hydrogen chloride, and then it was stirred at 55° C. for about 20 hours. The reaction mixture was allowed to cool and then it was poured onto 500 mL of ice. The resultant mixture was basified with 50% sodium hydroxide and extracted once with 300 mL of ethyl acetate. The extract was washed three times with 80 mL brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to a residue, yielding 5.14 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto cool
  2. extractionextracted once with 300 mL of ethyl acetate
  3. washThe extract was washed three times with 80 mL brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue

Sources & evidence

ORD record
ord-de3271b3ac3d47ac944b3b23406fb15e
Source dataset
uspto-grants-2012_02
Patent number
US08119563B2

Reaction notes

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