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

HRID 1678356Notes

Reaction equation

HRID 1678356 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-263b5905f07245d9ad12595c1d99804b
Source dataset
uspto-grants-2011_08
Patent number
US08008278B2

Reaction notes

Loading…