Pyrrolidine → 2-(Pyrrolidin-1-ylmethyl)pyridine

HRID 262951Notes

Reaction equation

HRID 262951 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>C(#N)C>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 5642092-(Bromomethyl)pyridine

Product 1

HCID 14390642-(Pyrrolidin-1-ylmethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 20.0 g (0.124 mole) of 1-(2-picolyl)pyrrolidine, obtained via the alkylation of 2-bromomethylpyridine with pyrrolidine, in 100 ml acetonitrile was added one equivalent of cyanomethyl benzenesulfonate in 50 ml acetonitrile maintaining the temperature at about 25°. After the addition was complete, the reaction was stirred at room temperature for 18 hours. The acetonitrile was removed under reduced pressure and tetrahydrofuran was added. The crystalline product was collected by filtration and washed with tetrahydrofuran and ether. After air drying, the yield of colorless crystals was 38.5 g (86%), m.p. 118.5°-120°.

Sources & evidence

ORD record
ord-df0cf71bd8f84f0b9981e06d33a57a05
Source dataset
uspto-grants-1979_05
Patent number
US04155909

Reaction notes

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