HCID 66587487, compound → 4-(Piperidin-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

HRID 625398Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[B:16]1[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]1)([O-])=O>C(OCC)(=O)C.[C].[Pd]>[N:10]1([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[C:5]([B:16]3[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]3)[CH:6]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

Conditions

Temperature: 5 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 1-(4-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine (600.0 mg, 1.81 mmol, 1.00 equiv) in ethyl acetate (30.0 mL), then Palladium carbon (10%) (150 mg) was added next. The gas of H2 was introduced in. The resulting solution was stirred for 1 h at 0=5° C. The Pd/C was filtered out and the filtrate was collected and concentrated under vacuum. This resulted in 545.8 mg (99%) of 4-(piperidin-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine as a green to yellow solid. The target product was unstable, it was used to the next reaction step rapidly

Workup

customInto a 50-mL round-bottom flask, was placed
additionThe gas of H2 was introduced in
filtrationThe Pd/C was filtered out
customthe filtrate was collected
concentrationconcentrated under vacuum
customThis resulted in 545.8 mg (99%) of 4-(piperidin-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine as a green to yellow solid
customit was used to the next reaction step rapidly

Sources & evidence

ORD record: ord-4b0d7701179140528fa43ab0af1eeca1
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09301951B2

Reaction notes

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