4-Chlorobenzonitrile → 4-(1-pyrrolidinyl)benzonitrile

HRID 1505165Notes

Reaction equation

HRID 1505165 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 121634-ChlorobenzonitrileHCID 31268Pyrrolidine

Product 1

HCID 49612714-(1-pyrrolidinyl)benzonitrileYield 33%

Conditions

Temperature
100 °C

Procedure

To commercially available 4-chlorobenzonitrile 17 (5 g, 36 mmol) 12 ml of pyrrolidine were added and the reaction was heated at 100° C. for 24 hours in closed vessel. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The purification of the crude residue by chromatographic column using AcOEt 1/Petroleum ether 9 as eluant gave 1.68 g of a pale yellow solid. Yield=33% 1HNMR (DMSO, 200 MHz) δ 1.96 (4H, m), 3.28 (4H, m), 6.58 (2H, d, J=9 Hz), 7.51 (2H, d, J=9 Hz)

Workup

  1. customThe reaction was evaporated
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with water and brine
  4. customThe purification of the crude residue by chromatographic column

Sources & evidence

ORD record
ord-ce869e67e7f94ed1a50fdba6456bb80f
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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