Ammonia → Benzyl 4-sulfamoylpiperidine-1-carboxylate

HRID 1914714Notes

Reaction equation

[NH3:1].[CH2:2]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([S:18](Cl)(=[O:20])=[O:19])[CH2:14][CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1.CO>[NH2:1][S:18]([CH:15]1[CH2:16][CH2:17][N:12]([C:10]([O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:11])[CH2:13][CH2:14]1)(=[O:20])=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Dioxane (250 mL) is saturated with ammonia and cooled down to 0° C. A solution of benzyl-4-(chlorosulfonyl)piperidine-1-carboxylate (10 g; 31.5 mmol; 1 eq) in dioxane (25 mL) is added dropwise over 10 min. The reaction mixture is stirred at room temperature for 3 h while keeping ammonia bubbling. The suspension is filtered through a short plug of silica using dioxane as eluent and the resulting solution is concentrated in vacuo to give a colourless oil. The oil is taken up in MeOH and concentrated in vacuo to give a white foam which is crystallised from EtOAc and Et2O to afford 8.1 g (86%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.40-7.29 (m, 5H), 6.79 (s, 2H), 5.08 (s, 2H), 4.10 (br d, J=13.3 Hz, 2H), 3.05 (tt, J=11.9, 3.6 Hz, 1H), 2.95-2.75 (m, 2H), 2.0 (dd, J=1.8, 11.5 Hz, 2H), 1.46 (dq, J=12.5, 4.4 Hz, 2H). HPLC (max plot) 82%; Rt 3.55 min.

Workup

filtrationThe suspension is filtered through a short plug of silica
concentrationthe resulting solution is concentrated in vacuo
customto give a colourless oil
concentrationconcentrated in vacuo
customto give a white foam which
customis crystallised from EtOAc and Et2O

Sources & evidence

ORD record: ord-e21a5d28a69241faba2d84994170a06d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614215B2

Reaction notes

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