Hydrochloric Acid → N-tert-butyl-1-benzhydryl-3-methylazetidin-3-amine hydrochloride

HRID 473999Notes

Reaction equation

CS(O[C:6]1([CH3:23])[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25].[ClH:29]>C(O)(C)C.CCOCC>[ClH:29].[C:24]([NH:28][C:6]1([CH3:23])[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)([CH3:27])([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-benzhydryl-3-methylazetidin-3-yl methanesulfonate (2.00 g, 6.23 mmol) in iso-propanol (10 ml) was added tert-butyl amine (1.36 g, 18.63 mmol). The mixture was heated at 80° C. for 3 h. The reaction mixture was then allowed to cool to room temperature and concentrated. The residue was slurried with ethyl acetate and filtered, washing with further ethyl acetate and then concentrated to give a solid. The solid was slurried in ether and hydrochloric acid (20 ml, 2M in ether) was added, then stirred for 10 mins and filtered to provide the title compound as a tan solid (1.69 g, 74%). 1H NMR (DMSO) 1.40 (9H, s), 1.99 (3H, s), 3.85 (2H, brs), 4.11 (2H, brs), 4.71 (1H, brs), 7.35-7.50 (6H, m), 7.70-7.81 (4H, m), 10.23 (1H, s).

Workup

temperatureto cool to room temperature
concentrationconcentrated
filtrationfiltered
washwashing with further ethyl acetate
concentrationconcentrated
customto give a solid
filtrationfiltered

Sources & evidence

ORD record: ord-6f201b58f4dd44f8aff34c55cb9a9437
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637511B2

Reaction notes

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