(4-Bromophenyl)boronic acid → 1-(1-(4-Bromophenyl)piperidin-4-yl)-4-methylpiperazine

HRID 472307Notes

Reaction equation

HRID 472307 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[Br:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N:11]2[CH2:12][CH2:13][CH:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[CH2:9][CH2:10]2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 79599(4-Bromophenyl)boronic acidHCID 7957071-Methyl-4-(piperidin-4-yl)piperazine

Product 1

HCID 674790211-(1-(4-Bromophenyl)piperidin-4-yl)-4-methylpiperazine

Procedure

1-[1-(4-Bromo-phenyl)-piperidin-4-yl]-4-methyl-piperazine was prepared from 1-methyl-4-piperidin-4-yl-piperazine (0.50 g, 2.7 mmol) and 4-bromobenzeneboronic acid (0.50 g, 2.5 mmol) in a manner analogous to Step 49a. The reaction product isolated as a tan solid (0.077 g, 9%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.32 (d, J=7.9 Hz, 2H), 6.79 (d, J=7.7 Hz, 2H), 3.72-3.65 (m, 2H), 2.85-2.35 (m, 14H), 2.00-1.90 (m, 2H), 1.73-1.60 (m, 2H). MS=338, 340 (MH)+.

Sources & evidence

ORD record
ord-a5b3cb7fafe84608a079412b4325e1d7
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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