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

HRID 499071
Notes
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Reaction equation

HRID 499071 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 100652951-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

Product 1

HCID 68457650N-tert-butyl-1-benzhydryl-3-methylazetidin-3-amine hydrochlorideYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
HCID 3776
Isopropanol
Solvent

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

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washwashing with further ethyl acetate
  5. concentrationconcentrated
  6. customto give a solid
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e4b12d375e1b44638b15b7c8a4dcec43
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07767672B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes