Piperidine, 1-(2-chloroethyl)-, hydrochloride → 1-[2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl]piperidine

HRID 885937Notes

Reaction equation

HRID 885937 reaction equation
[NH:1]1[CH:5]=[C:4]([B:6]2[O:14][C:11]([CH3:13])([CH3:12])[C:8]([CH3:10])([CH3:9])[O:7]2)[CH:3]=[N:2]1.Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH3:12][C:11]1([CH3:13])[C:8]([CH3:9])([CH3:10])[O:7][B:6]([C:4]2[CH:3]=[N:2][N:1]([CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:5]=2)[O:14]1

Participants

3

Reactant 2

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride2×HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 593203891-[2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl]piperidine

Conditions

Temperature
90 °C

Procedure

The title compound was prepared from pyrazole-4-boronic acid pinacol ester and 1-(2-chloroethyl)piperidine hydrochloride according to Method AC (heating to 90° C. for 6 days before addition of further 1-(2-chloroethyl)piperidine hydrochloride, and heating to 90° C. for a further 3 days) and was isolated as a brown gum (69%). LCMS (ES+) 305 (M+H)+, RT 1.91 minutes (Method 1).

Sources & evidence

ORD record
ord-be10d9de99ac49fe9d65c7643f8c1669
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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