Acetyl chloride → HCID 66745655, compound

HRID 591669Notes

Reaction equation

HRID 591669 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[C:29](Cl)(=[O:31])[CH3:30]>C(Cl)Cl>[CH2:1]([N:8]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[C:29](=[O:31])[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 15380687tert-Butyl 4-(benzylamino)piperidine-1-carboxylate

Product 1

HCID 66745655HCID 66745655, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(benzylamino)piperidine-1-carboxylate (8.1 g, 28.0 mmol) and Et3N (7.8 mL, 56.0 mmol) in CH2Cl2 (100 mL) was added acetyl chloride (2.4 mL, 33.5 mmol) and the reaction was stirred at room temperature overnight, then concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 30% to 60% EtOAc/CH2Cl2, afforded tert-butyl 4-(N-benzylacetamido)piperidine-1-carboxylate (9.3 g, 99%).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by flash chromatography on silica gel
  3. washeluting with 30% to 60% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-b91a1f35e9944419b41a872be95e4802
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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