Hydrochloric Acid → 2-Hydroxy-2-(1-benzylpyrrolidin-3-yl)acetonitrile

HRID 2050187

Reaction equation

HRID 2050187 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C-:16]#[N:17].[K+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O>[OH:14][CH:13]([CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)[C:16]#[N:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 45894781-Benzylpyrrolidine-3-carbaldehyde

Product 1

HCID 203422572-Hydroxy-2-(1-benzylpyrrolidin-3-yl)acetonitrileYield 84.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 12.45 g of crude 1-benzyl-3-formylpyrrolidine in a mixture of 23 ml of tetrahydrofuran and 23 ml of water is added 11.4 ml (2 equivalents) of concentrated hydrochloric acid and then 8.39 g (2 equivalents) of potassium cyanide powder in a period of 15 minutes under ice-cooling. The mixture is stirred at the same temperature for 2 hours, adjusted to pH 10 with 10% aqueous sodium carbonate solution, and extracted thrice with methylene chloride. The extract is washed with water, dried over sodium sulfate and evaporated under reduced pressure to yield 12.05 g of 2-hydroxy-2-(1-benzylpyrrolidin-3-yl) acetonitrile.

Workup

  1. extractionextracted thrice with methylene chloride
  2. washThe extract is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5299a62f2b5842b290a5b4acde50e4c2
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Linked notes

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