Hydrochloric Acid → ((S)-1-benzylpyrrolidin-3-yl)diphenylacetonitrile hydrochloride

HRID 1171993Notes

Reaction equation

HRID 1171993 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]#[N:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:28]>C(OC(C)C)(=O)C>[ClH:28].[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:14]#[N:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13633739((S)-1-Benzylpyrrolidin-3-yl)diphenylacetonitrile

Product 1

HCID 66855790((S)-1-benzylpyrrolidin-3-yl)diphenylacetonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

The product of step (b) above was dissolved in isopropyl acetate (ca. 1 g/10 mL) and the solution was mixed with an equal volume of 1N aqueous hydrochloric acid. The resulting layers were separated and the aqueous layer was extracted with an equal volume of isopropyl acetate. The organic layers were combined, dried over sodium sulfate and filtered. The solvent was removed in vacuo to afford ((S)-1-benzylpyrrolidin-3-yl)diphenylacetonitrile hydrochloride as a foamy solid. (Note: This hydrochloride salt can also be prepared during the work-up of Step (b)).

Workup

  1. customThe resulting layers were separated
  2. extractionthe aqueous layer was extracted with an equal volume of isopropyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-875ca7904c914f5ab950c27d27508533
Source dataset
uspto-grants-2010_11
Patent number
US07829728B2

Reaction notes

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