Pyrrolidine → 7-Benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinoline

HRID 2415461Notes

Reaction equation

HRID 2415461 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 22641419HCID 22641419, compound

Product 1

HCID 226413107-Benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinolineYield 75%

Conditions

Temperature
80 °C

Procedure

A mixture of 534 mg (1.8 mmol) of 7-benzyloxy-4-chloro-2-methyl-quinoline and 3.77 ml (45 mmol) pyrrolidine was heated at 80° C. (oil bath temperature) under an argon atmosphere for 23 h after which time the reaction was completed according to HPLC analysis. The reaction was partitioned between EtOAc and water, the aqueous layer was extracted once with EtOAc, the combined organic layers were washed with water then saturated NaCl solution, dried over magnesium sulphate and concentrated in vacuo. The residue was applied to silica gel column with CH2Cl2/MeOH/NH4OH (19:1:0.05) as eluent. Combination of the purified fractions and concentration in vacuo gave 430 mg (74.5%) of the 7-benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinoline as a brown solid. ISP mass spectrum, m/e: 319.4 (M+1 calculated for C21H22N2O: 319).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. extractionthe aqueous layer was extracted once with EtOAc
  3. washthe combined organic layers were washed with water
  4. dry with materialsaturated NaCl solution, dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-3ab863c303974bf4a2cfcb35259e93bc
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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