1-Bromodecane → 1-Decylpyrrolidin-2-one

HRID 1155104Notes

Reaction equation

HRID 1155104 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[NH:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17].CC([O-])(C)C.[K+]>CS(C)=O>[CH2:2]([N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 81731-BromodecaneHCID 120252-PyrrolidoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 1714271-Decylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

22.1 g 1-Bromodecane (0.1 mol), 8.5 g (0.1 mol) of 2-pyrrolidone and 11.2 g (0.1 mol) of potassium tert-butylate were stirred in 100 ml of absolute DMSO for one hour. The DMSO was removed under reduced pressure, the residue taken up with diethyl ether, and washed with water (2 times). After drying with anhydrous MgSo4 and evaporating, the residue was distilled in vacuo. A first fraction, boiling between 140° and 147° C./1.2 mm Hg was discarded. The second fraction 17.4 g of pure product, b.p. 148° C./1.2 mm Hg.

Workup

  1. customThe DMSO was removed under reduced pressure
  2. washwashed with water (2 times)
  3. customAfter drying with anhydrous MgSo4
  4. customevaporating
  5. distillationthe residue was distilled in vacuo
  6. customboiling between 140° and 147° C.

Sources & evidence

ORD record
ord-70989bcb84964edaa37a7e890bb5524a
Source dataset
uspto-grants-1981_11
Patent number
US04299840

Reaction notes

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