Hydrochloric Acid → 4-Piperidin-1-ylmethyl-benzylamine

HRID 1191004Notes

Reaction equation

HRID 1191004 reaction equation
[N:1]1([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CCOCC>[Pd].CO>[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:12][NH2:13])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 75376034-(piperidin-1-ylmethyl)benzonitrile

Product 1

HCID 52002924-Piperidin-1-ylmethyl-benzylamineYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add 4-(piperidin-1-ylmethyl)-benzonitrile (890 mg, 4.45 mmol), 2M hydrogen chloride in ether (8.9 mL, 17.8 mmol) and 10% Pd/C (90 mg) to methanol (100 mL) in a pressure vessel. Flush the vessel three times with hydrogen and charge to 50 psi with hydrogen. Stir at room temperature for 2 h. Filter the catalyst through Celite® and concentrate the filtrate in vacuo. Purify by chromatography on silica gel (100 g) eluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound as a colorless oil (0.82 g, 90%). MS (ES+) m/z: 205 (M+H)+.

Workup

  1. customFlush the vessel three times with hydrogen
  2. additioncharge to 50 psi with hydrogen
  3. filtrationFilter the catalyst through Celite®
  4. concentrationconcentrate the filtrate in vacuo
  5. customPurify by chromatography on silica gel (100 g)
  6. washeluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-496deacabee746ba8cfbcbc9213e3ce0
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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