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

HRID 279276Notes

Reaction equation

HRID 279276 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:3])[NH2:2].Cl.[OH-:18].[Na+]>B.C1COCC1>[CH2:1]([OH:3])[CH2:4][CH3:8].[OH2:18].[NH4+:2].[OH-:3].[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

6

Reactant 3

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

Product 2

HCID 147090362-(Aminomethyl)-1-(4-chlorobenzyl)pyrrolidineYield 86%HCID 131723153PrOH-H2O NH4OH

Reagents, catalysts & solvents 1

HCID 2723981Borane;tetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

2-carbamoyl-1-(4-chlorobenzyl)pyrrolidine was dissolved in 1M BH3-THF (9.4 mL) and heated to 70° C. After 16 h and 25 h, additional 0.5 equiv. of 1M BH3-THF were added. After 40 h, 1 N aqueous HCl solution (14 mL) was added and the reaction was heated to reflux for 3 h, 3 N aqueous HCl solution (6 mL) was added and the reaction was heated for an additional 3 h. The reaction mixture was cooled to 25° C., basicified with 4 N aqueous NaOH solution and extracted with CH2Cl2 (4×15 mL). Chromatography (SiO2, 8:1:1 PrOH—H2O—NH4OH) afforded 2-(aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (1.21 g, 86%)

Workup

  1. waitAfter 40 h
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 3 h
  4. temperaturethe reaction was heated for an additional 3 h
  5. temperatureThe reaction mixture was cooled to 25° C.
  6. extractionextracted with CH2Cl2 (4×15 mL)

Sources & evidence

ORD record
ord-9ed4b0cc6e1e4186a69302c7618cb0ff
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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