Nitrogen → 5-Pyrrolidinoamylamine

HRID 1044807Notes

Reaction equation

HRID 1044807 reaction equation
N#N.Br[CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[N:9].[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CC#N.CCO.[Ni]>[N:10]1([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH2:9])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

8

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 794355-Bromopentanenitrile

Product 1

HCID 70191825-Pyrrolidinoamylamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 5-bromovaleronitrile (0.21 mL, 1.80 mmol), pyrrolidine (0.15 mL, 1.81 mmol), K2CO3 (498 mg, 3.60 mmol) and KI (60 mg, 0.36 mmol) in dry CH3CN (15 mL) was refluxed for 1 h. The mixture was filtered and concentrated under reduced pressure. A 0.05 mol/L solution of the crude nitrile (59 mg, 0.39 mmol) in EtOH (8 mL) was hydrogenated at rt using the H-Cube® (1 mL/min) with a Raney Nickel cartridge (30 mm) under 50 bar until completion of the reaction. The solution was then concentrated under reduced pressure to give crude 5-(pyrrolidin-1-yl)pentan-1-amine as a colorless oil. LC-MS-conditions 01: tR=0.16 min; [M+H]+=157.19.

Workup

  1. temperaturewas refluxed for 1 h
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customwas hydrogenated at rt
  5. customuntil completion of the reaction
  6. concentrationThe solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-da4202b077e04a73a700f324f39e291e
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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