Acetyl chloride → HCID 66745169, compound

HRID 591653Notes

Reaction equation

HRID 591653 reaction equation
[CH:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)([CH3:3])[CH3:2].CCN(CC)CC.[C:25](Cl)(=[O:27])[CH3:26]>C(Cl)Cl>[CH:1]([N:4]([CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:9][CH2:10]1)[C:25](=[O:27])[CH3:26])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 20801236tert-Butyl 4-[(propan-2-yl)amino]piperidine-1-carboxylate

Product 1

HCID 66745169HCID 66745169, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of tert-butyl 4-(isopropylamino)piperidine-1-carboxylate (1.2 g, 5.19 mmol) in CH2Cl2 (18 mL) was added Et3N (1.44 mL, 10.38 mmol) followed by acetyl chloride (0.55 mL, 7.78 mmol). The resulting solution was stirred for 2.5 hours, then concentrated in vacuo. The material was purified by flash chromatography on silica gel, eluting with 0% to 5% of EtOAc/CH2Cl2, to afford tert-butyl 4-(N-isopropylacetamido)piperidine-1-carboxylate (0.88 g, 59%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe material was purified by flash chromatography on silica gel
  3. washeluting with 0% to 5% of EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-060ac4bd04dc4d37ab025f0b7a3d2459
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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