Pyrrolidine → HCID 22641362, compound

HRID 2415478Notes

Reaction equation

HRID 2415478 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](Cl)=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[CH2:21][CH2:22][CH2:23][CH3:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH2:2]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[CH2:21][CH2:22][CH2:23][CH3:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 22641405HCID 22641405, compound

Product 1

HCID 22641362HCID 22641362, compoundYield 101.2%

Procedure

A solution of 1 g (3.07 mmol) of 7-benzyloxy-6-butyl-4-chloro-quinoline hydrochloride in 2.5 ml (30.7 mmol) of pyrrolidine was heated at 60° C. with stirring under an argon atmosphere for 24 h after which time the reaction was completed according to HPLC analysis. The excess pyrrolidine was evaporated off, and the residue was partitioned between EtOAc and water. The layers were separated and the aqueous layer once extracted with AcOEt. The combined organic layers were washed with water then saturated NaCl solution, dried over magnesium sulphate and concentrated in vacuo to give 1.12 g (97.4%) of the 7-benzyloxy-6-butyl-4-pyrrolidin-1-yl-quinoline as a brown oil. ISP mass spectrum, m/e: 361.3 (M+1 calculated for C24H28N2O: 361).

Workup

  1. customThe excess pyrrolidine was evaporated off
  2. customthe residue was partitioned between EtOAc and water
  3. customThe layers were separated
  4. extractionthe aqueous layer once extracted with AcOEt
  5. washThe combined organic layers were washed with water
  6. dry with materialsaturated NaCl solution, dried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e058e63c88e485cb2de87c08f12ee83
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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