Propionyl chloride → HCID 21904439, compound

HRID 1839190Notes

Reaction equation

HRID 1839190 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:22](=[O:25])[CH2:23][CH3:24])[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 21904427HCID 21904427, compound

Product 1

HCID 21904439HCID 21904439, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-Boc-piperidin-3-ylmethyl)-N-(pyridin-3-yl) amine 17 (100 mg, 0.34 mmol) and piperidinomethyl polystyrene resin (100 mg) in 1 mL of dry CH2Cl2 was added propionyl chloride (30 μL, 1 eq.) at room temperature. After being shaken at room temperature overnight, the reaction mixture was passed through an aminopropyl NH2 cartridge and washed with CH2Cl2. Removal of CH2Cl2 afforded N-(1-Boc-piperidin-3-ylmethyl)-N-(pyridin-3-yl)propionamide 18 (85 mg, 71%). LRMS 248 (M−100)+.

Workup

  1. washwashed with CH2Cl2
  2. customRemoval of CH2Cl2

Sources & evidence

ORD record
ord-175e0f90316e4a66bb7a52147818dd55
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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