Hydrochloric Acid → (S)-(3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine hydrochloride

HRID 509331Notes

Reaction equation

[C:1]([C:4]1[C:5]([C@@H:10]([NH:21]C(=O)OC(C)(C)C)[C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)#[C:2][CH3:3].[ClH:29]>C(Cl)Cl>[ClH:29].[C:1]([C:4]1[C:5]([C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=2)[NH2:21])=[N:6][CH:7]=[CH:8][CH:9]=1)#[C:2][CH3:3]

Participants

Conditions

Temperature: 23 °C

Procedure

To a 500 mL round bottom flask containing (S)-tert-butyl ((3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate (400 mg, 1.025 mmol) was added DCM (8 mL) and the mixture was stirred at 23° C. for 2 min. At this time, hydrogen chloride (4N in 1,4-dioxane) (37.4 mg, 1.025 mmol) (4 mL) was added via syringe. The reaction was stirred for 3 h then the volatiles were removed via rotoryevaporator. The solid was placed on high vacuum overnight to give (S)-(3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)-methanamine hydrochloride as a white solid.

Workup

stirringThe reaction was stirred for 3 h
customthe volatiles were removed via rotoryevaporator
customwas placed on high vacuum overnight

Sources & evidence

ORD record: ord-02dc67b7a5ef45c18e7b6a5b0b56c5b4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096527B2

Reaction notes

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