Dichloromethane → 380901-64-4

HRID 1826602Notes

Reaction equation

HRID 1826602 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[OH-].[Na+].[CH2:18](Cl)Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[N+:1]([CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[C-:18]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 22135013380901-64-4Yield 35%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a solution of 4-aminomethyl-1-Boc-piperidine (77.1 g, 360 mmol, 1 equiv) in 108 mL of methylene chloride at room temperature (rt) was added benzyltriethylammonium chloride (1.64 g, 72 mmol, 0.2 equiv) followed by 108 mL of a 50% sodium hydroxide solution. The reaction spontaneously achieved a mild reflux for 1.5 h and was allowed to stir for an additional 12 h at rt. The reaction was diluted with H2O and the product was extracted into methylene chloride. The organic layer was dried over anhydrous potassium carbonate, filtered, and concentrated. The crude residue was passed through a pad of silica gel with a 2:1 EtOAc:hexane solution. Evaporation of the eluent provided 28.0 g (35%) the title compound.

Workup

  1. customThe reaction
  2. temperaturea mild reflux for 1.5 h
  3. extractionthe product was extracted into methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customEvaporation of the eluent

Sources & evidence

ORD record
ord-82ef7c5741d749f5a5a2d025f5054b1b
Source dataset
uspto-grants-2006_05
Patent number
US07053078B2

Reaction notes

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