Hydrochloric Acid → HCID 13431749, compound

HRID 638192Notes

Reaction equation

B(Cl)(Cl)Cl.[NH:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:19](#N)[CH3:20].Cl.[OH2:23]>ClC(Cl)C>[C:19]([C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:5][CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)(=[O:23])[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 2.03M solution of boron trichloride (20×1.2 mmol) in dichloroethane (11.8 ml) is dropwise added a solution of 4-anilino-1-methylpiperidine (3.81 g, 20 mmol) in dichloroethane (38 ml), and acetonitrile (2.1 ml, 20×1.2 mmol) is added to the mixture, which is heated under reflux over a period of 20 hours. After cooling, the reaction mixture is mixed with 2N hydrochloric acid (15 ml) and water (30 ml) and stirred at 100° C. over a period of 20 minutes. After cooling, the reaction mixture is mixed with conc. aqueous ammoniac solution and separated. The organic layer is washed with water, dried over anhydrous potassium carbonate and concentrated in vacuo to give 4-(2-acetylanilino)-1-methylpiperidine (4.41 g) as an oil. The yield is 95%.

Workup

additionis added to the mixture, which
temperatureis heated
temperatureunder reflux over a period of 20 hours
temperatureAfter cooling
temperatureAfter cooling
additionthe reaction mixture is mixed with conc. aqueous ammoniac solution
customseparated
washThe organic layer is washed with water
dry with materialdried over anhydrous potassium carbonate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-beddad01415a4300a471ffd3d614ce74
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04560684

Reaction notes

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