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

HRID 1829776Notes

Reaction equation

HRID 1829776 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 3h. 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 3h
  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-9d020071ca4343eba74c89d99f5d6c25
Source dataset
uspto-grants-2006_06
Patent number
US07064134B2

Reaction notes

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