Acetyl chloride → Tert-butyl 4-(4-acetamidophenylthio)piperidine-1-carboxylate

HRID 624278Notes

Reaction equation

HRID 624278 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>ClCCl.O>[C:29]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18538812Tert-butyl 4-(4-aminophenylthio)piperidine-1-carboxylate

Product 1

HCID 68752092Tert-butyl 4-(4-acetamidophenylthio)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a 10 mL round-bottomed flask was added tert-butyl 4-(4-aminophenylthio)piperidine-1-carboxylate (100 mg, 0.324 mmol) and triethylamine (249 μl, 1.783 mmol) in dichloromethane (3242 μl). The mixture was cooled to −78° C. and acetyl chloride (115 μl, 1.621 mmol) was added. The solution was warmed to room temperature, stirred for 1 h and then diluted with water and additional dichloromethane. The aqueous phase was extracted twice with dichloromethane and the combined organics were dried with sodium sulfate, filtered and concentrated to give the title compound.

Workup

  1. temperatureThe solution was warmed to room temperature
  2. extractionThe aqueous phase was extracted twice with dichloromethane
  3. dry with materialthe combined organics were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b2f3763f6c3244079a729d30c90f60d0
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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