Nitrogen → HCID 66819967, compound

HRID 1044811Notes

Reaction equation

HRID 1044811 reaction equation
N#N.[CH3:3][O:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][NH:7]1.Br[CH2:12][CH2:13][CH2:14][C:15]#[N:16].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:3][O:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16]

Participants

6

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 1439532-(Methoxymethyl)pyrrolidine

Product 1

HCID 66819967HCID 66819967, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-(methoxymethyl)pyrrolidine (300 mg, 2.61 mmol) and 4-bromobutyronitrile (0.31 mL, 2.99 mmol) in dry CH3CN (13 mL) was added K2CO3 (1.51 g, 10.94 mmol) at rt followed by KI (43 mg, 0.26 mmol). The reaction mixture was stirred at rt for 15 h. The mixture was filtered and the filtrate partitioned between water and CH2Cl2. The layers were separated and the aq. layer extracted with CH2Cl2 (3×). The combined org. extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The crude nitrile was redissolved in dry THF (21 mL) and treated with LiALH4 (192 mg, 5.07 mmol) at 0° C. The reaction mixture was warmed up to rt and stirred at this temperature until completion of the reaction. Sat. aq. Rochelle's salt solution and EA were then added, the layers separated and the aq. layer extracted with EA (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give crude 4-(2-(methoxymethyl)pyrrolidin-1-yl)butan-1-amine as a pale yellow oil. GC-MS-conditions 01: tR=2.1 min; [M+H]+=187.20.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate partitioned between water and CH2Cl2
  3. customThe layers were separated
  4. extractionthe aq. layer extracted with CH2Cl2 (3×)
  5. dry with materialextracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe crude nitrile was redissolved in dry THF (21 mL)
  9. additiontreated with LiALH4 (192 mg, 5.07 mmol) at 0° C
  10. temperatureThe reaction mixture was warmed up to rt
  11. stirringstirred at this temperature until completion of the reaction
  12. additionSat. aq. Rochelle's salt solution and EA were then added
  13. customthe layers separated
  14. extractionthe aq. layer extracted with EA (3×)
  15. washThe combined organic extracts were washed with brine
  16. dry with materialdried over MgSO4
  17. filtrationfiltered
  18. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-e0ebb7f6bf4f4475b1ebe75848628bab
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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