Hydrochloric Acid → 2-(Aminomethyl)-1-(4-chlorobenzyl)pyrrolidine

HRID 133571Notes

Reaction equation

HRID 133571 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)(=O)[NH2:2].Cl.[OH-].[Na+]>B.C1COCC1>[NH2:2][CH2:1][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 184262722-Carbamoyl-1-(4-chlorobenzyl)pyrrolidine

Product 1

HCID 147090362-(Aminomethyl)-1-(4-chlorobenzyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 2723981Borane;tetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

2-Carbamoyl-1-(4-chlorobenzyl)pyrrolidine was dissolved in 1 M BH3-THF (9.4 mL), and the resulting solution was heated at 70° C. A 1 M BH3-THF (0.5 equivalent) was further added twice after 16 hours and 25 hours. After 40 hours, a 1 M hydrochloric acid was added, and the resulting mixture was refluxed for 3 hours. A 3 M hydrochloric acid (6 mL) was added, and the reaction product was stirred for another 3 hours with heating, then cooled to 25° C., alkalinized with a 6 M aqueous solution of NaOH and extracted with dichloromethane (4×15 mL). The obtained crude product was purified by chromatography (SiO2, PrOH/H2O/NH4OH=8:1:1) to thereby afford 2-(aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (1.21 g, 86%).

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. temperaturewith heating
  3. temperaturecooled to 25° C.
  4. extractionextracted with dichloromethane (4×15 mL)
  5. customThe obtained crude product
  6. customwas purified by chromatography (SiO2, PrOH/H2O/NH4OH=8:1:1) to thereby afford 2-(aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (1.21 g, 86%)

Sources & evidence

ORD record
ord-4ba10e79310d4d64b5039717c1cc59dc
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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