4-Benzylpiperidine → 4-(4-Benzylpiperidin-1-yl)-5-bromo-3-nitropyridin-2-amine

HRID 416867Notes

Reaction equation

HRID 416867 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:11]2[CH2:16][CH2:15]N(CC(NC3SC=CN=3)=O)[CH2:13][CH2:12]2)[C:5]([Br:26])=[CH:4][N:3]=1.BrC1C(Cl)=C([N+]([O-])=O)C(N)=NC=1.CCN(C(C)C)C(C)C.[CH2:48]([CH:55]1CCNCC1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(O)(C)C>[CH2:48]([CH:55]1[CH2:13][CH2:12][N:11]([C:6]2[C:5]([Br:26])=[CH:4][N:3]=[C:2]([NH2:1])[C:7]=2[N+:8]([O-:10])=[O:9])[CH2:16][CH2:15]1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

6

Reactant 4

HCID 317384-BenzylpiperidineHCID 81531DiisopropylethylamineHCID 454802365-Bromo-4-chloro-3-nitropyridin-2-amineHCID 468678032-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

Product 1

HCID 578971604-(4-Benzylpiperidin-1-yl)-5-bromo-3-nitropyridin-2-amineYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

This was prepared using the same procedure as for 2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide, but here using 5-bromo-4-chloro-3-nitropyridin-2-amine (1.00 g, 3.96 mmol), DIPEA (3.5 eq, 13.86 mmol, 2.41 mL), isopropanol (20 mL) and 4-benzylpiperidine (1.1 eq, 4.36 mmol, 0.77 mL). Concentration in vacuo to half volume after 18 h gave a bright yellow solid, which was filtered and washed with cold water (2×5 mL) to give the product (1.12 g, 72%) as a yellow solid; δH (500 MHz, DMSO-d6) 1.38 (qd, br, J=12.2, 3.5 Hz, 2H, 2× piperidine CHAHB), 1.60 (d, br, J=10.9 Hz, 2H, 2× piperidine CHAHB), 1.69-1.76 (m, 1H, piperidine CH), 2.55 (d, J=7.1 Hz, 2H, 2× piperidine NCHAHA), 2.74 (t, br, J=11.9 Hz, 2H, 2× piperidine NCHAHA), 3.22 (d, br, J=12.5 Hz, 2H, PhCH2), 6.93 (s, br, 2H, NH2), 7.16-7.18 (1H, m, phenyl H-4), 7.19 (d, J=7.4 Hz, 2H, phenyl H-2 & H-6), 7.28 (t, J=7.1 Hz, 2H, phenyl H-3 & H-5), 8.13 (s, 1H, pyridine H-6);

Workup

  1. customThis was prepared
  2. concentrationConcentration in vacuo to half volume after 18 h
  3. customgave a bright yellow solid, which
  4. filtrationwas filtered
  5. washwashed with cold water (2×5 mL)

Sources & evidence

ORD record
ord-8780d55a10d7432d93671384d66b1039
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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