Piperidine → HCID 66782117, compound

HRID 1952302Notes

Reaction equation

HRID 1952302 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>CN1CCCC1=O>[Br:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2[N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 66782117HCID 66782117, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4-chloro-6-bromoquinoline (726 mg, 3 mmol) in 3 mL of 1-methyl-2-pyrrolidinone was added piperidine (510 mg, 6 mmol). The reaction was heated to 150° C. for 5 h. The solvents were removed in vacuo at 100° C. and the residue dissolved in methylene chloride and washed with water. The methylene chloride was dried with sodium sulfate and concentrated. The residue was triturated with hexane and the solid filtered off to give 6-bromo-4-(1-piperidinyl)quinoline (877 mg, 73%).

Workup

  1. customThe solvents were removed in vacuo at 100° C.
  2. dissolutionthe residue dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialThe methylene chloride was dried with sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was triturated with hexane
  7. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-eb66fb5e56d14bc9a632b54286eba39d
Source dataset
uspto-grants-2013_03
Patent number
US08404837B2

Reaction notes

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