Water → 2-(Benzyloxy)-6-(pyrrolidin-1-yl)pyridine

HRID 1516148Notes

Reaction equation

HRID 1516148 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.O>C(OCC)(=O)C.CCCCCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 8174752-Benzyloxy-6-bromopyridine

Product 1

HCID 669701082-(Benzyloxy)-6-(pyrrolidin-1-yl)pyridineYield 95.3%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

In a dried microwave reactor, 526 mg (2.0 mmol) of 2-(benzyloxy)-6-bromopyridine and 1.70 ml (20 mmol) of pyrrolidine were placed, and the mixture was reacted using microwave at 150° C. for 10 min. The reaction mixture was mixed with 20 ml of water, extracted twice with 100 ml portions of ethyl acetate, and the organic layer was separated dried over anhydrous and kept under a reduced pressure to remove the solvent. The residue thus obtained was subjected to column chromatography using 10% ethyl acetate/hexane as an eluent to obtain 485 mg (yield 95%) of 2-(benzyloxy)-6-(pyrrolidin-1-yl)pyridine.

Workup

  1. customthe mixture was reacted
  2. customat 150° C.
  3. customfor 10 min
  4. extractionextracted twice with 100 ml portions of ethyl acetate
  5. customthe organic layer was separated
  6. customdried over anhydrous and
  7. customto remove the solvent
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-d635e4b5127f4322b36d4e1fd1bf724c
Source dataset
uspto-grants-2012_07
Patent number
US08227456B2

Reaction notes

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