Water → 1-(pyrrolidin-1-yl)hexan-1-one

HRID 1904179Notes

Reaction equation

HRID 1904179 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.O>C1C=CC=CC=1.N1C=CC=CC=1>[C:1]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 67340Hexanoyl chloride

Product 1

HCID 2468351-(pyrrolidin-1-yl)hexan-1-oneYield 80%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

Hexanoyl chloride (13.46 g, 0.1M) was added gradually to a cooled, stirred solution of pyrrolidine (7,25 g, 0.1M) in 200 ml of benzene and dry pyridine (7.91 g, 0.1M). Two hours after the addition water was added. The organic layer was washed successively with 5% aqueous hydrochloric acid, saturated sodium bicarbonate solution, and saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. Distillation of the residue gave 13.52 g (80%) of a colorless oil, b.p. 98-100/7 mm.

Workup

  1. additionwas added
  2. washThe organic layer was washed successively with 5% aqueous hydrochloric acid, saturated sodium bicarbonate solution, and saturated sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. distillationDistillation of the residue

Sources & evidence

ORD record
ord-7ef10fa8f14a4c96a0174c45d1942acc
Source dataset
uspto-grants-1989_06
Patent number
US04837026

Reaction notes

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