Sulfuric Acid → N-(1-benzyl-3-methylpyrrolidin-3-yl)acetamide

HRID 1948687Notes

Reaction equation

HRID 1948687 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH3:14])(O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:15]S(O)(=O)=O.[CH3:20][C:21]#[N:22]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH:22][C:21](=[O:15])[CH3:20])([CH3:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 186296481-Benzyl-3-methylpyrrolidin-3-OL

Product 1

HCID 13787481N-(1-benzyl-3-methylpyrrolidin-3-yl)acetamide

Procedure

A solution of 1-benzyl-3-methylpyrrolidin-3-ol (5.94 g, 31.1 mmol) in MeCN (200 mL) was cooled in an ice bath and conc H2SO4 (25 mL) was added dropwise over 15 min. The ice bath was allowed to melt and the mixture was stirred at rt over the weekend. The mixture was poured onto crushed ice (600 mL). The mixture was evaporated under reduced pressure to remove MeCN. Solid K2CO3 was added in portions to the residue until it was basic. The mixture was extracted with CH2Cl2 (3×150 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4 and concentrated to leave N-(1-benzyl-3-methylpyrrolidin-3-yl)acetamide (4.01 g).

Workup

  1. additionThe mixture was poured
  2. customThe mixture was evaporated under reduced pressure
  3. customto remove MeCN
  4. additionSolid K2CO3 was added in portions to the residue until it
  5. extractionThe mixture was extracted with CH2Cl2 (3×150 mL)
  6. washThe combined organic extracts were washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-604dda59a2e0424cb9e8c6ed71a573a9
Source dataset
uspto-grants-2013_03
Patent number
US08399504B2

Reaction notes

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