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

HRID 252096

Reaction equation

HRID 252096 reaction equation
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:17][CH2:16][C:15]([CH3:19])(O)[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-:21].[K+].[K+].[C:26](#[N:28])[CH3:27]>>[CH2:6]([N:13]1[CH2:17][CH2:16][C:15]([NH:28][C:26](=[O:21])[CH3:27])([CH3:19])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 186296481-Benzyl-3-methylpyrrolidin-3-OL

Product 1

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

Procedure

Add concentrated sulphuric acid (16 mL) dropwise to 1-benzyl-3-methyl-pyrrolidin-3-ol (4.4 g, 23 mmol) in acetonitrile (12 mL) at 0° C. Stir and allow the resulting solution to warm up gradually to room temperature overnight. Pour onto crushed ice and add saturated aqueous potassium carbonate and extract with dichloromethane. Combine the organic layers and wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give N-(1-benzyl-3-methylpyrrolidin-3-yl)-acetamide which may be used in the next step without further purification (4.89 g, 70%). 1H NMR (400 MHz, CDCl3) δ 7.22-7.34 (5H, m), 5.62 (1H, s), 3.57-3.66 (2H, m), 2.76-2.84 (2H, m), 2.54 (1H, td, J=8.80, 5.87 Hz), 2.47 (1H, d, J=9.78 Hz), 2.13 (1H, m), 1.90-1.93 (3H, m), 1.84-1.90 (1H, m), 1.49 (3H, s), MS (ES): m/z=233 [M+H].

Workup

  1. additionPour
  2. customonto crushed ice
  3. extractionextract with dichloromethane
  4. washwash with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-84ce6ce6bac146bb9fcaaa2cd5080ec9
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Linked notes

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