Pyrrolidine → 7-Benzyloxy-6-bromo-2-methyl-4-pyrrolidin-1-yl-quinoline

HRID 1743937Notes

Reaction equation

HRID 1743937 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][C:10]=1[Br:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][C:10]=1[Br:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 220545547-Benzyloxy-6-bromo-4-chloro-2-methyl-quinoline

Product 1

HCID 220545387-Benzyloxy-6-bromo-2-methyl-4-pyrrolidin-1-yl-quinolineYield 62.9%

Procedure

A mixture of 7-benzyloxy-6-bromo-4-chloro-2-methyl-quinoline (10.0 g, 27.6 mmol) and pyrrolidine (47 mL, 0.562 mol) was refluxed during 3 h. The mixture was cooled down and the pyrrolidine was evaporated under high vacuum. The residue was taken up in dichloromethane, washed with water and brine, dried over sodium sulfate, filtered and the solvents were evaporated under vacuum. 6.9 g of the title compound were obtained. Brown solid, ISP-MS: m/e=399.2 ([M+H]+).

Workup

  1. temperaturewas refluxed during 3 h
  2. temperatureThe mixture was cooled down
  3. customthe pyrrolidine was evaporated under high vacuum
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents were evaporated under vacuum

Sources & evidence

ORD record
ord-d22095912a2846448b1fe69b01ab9de7
Source dataset
uspto-grants-2006_03
Patent number
US07012073B2

Reaction notes

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