1-Benzylpiperazine → HCID 22174883, compound

HRID 1410381Notes

Reaction equation

HRID 1410381 reaction equation
[CH3:1][C:2]1[C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)=[C:5]([CH3:16])[N:4]([C:17]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:20]=[CH:19][N:18]=2)[N:3]=1.[CH2:29]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(Cl)Cl>[CH2:29]([N:36]1[CH2:41][CH2:40][N:39]([CH2:12][C:11]2[CH:14]=[CH:15][C:8]([O:7][C:6]3[C:2]([CH3:1])=[N:3][N:4]([C:17]4[N:22]=[C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=5)[CH:20]=[CH:19][N:18]=4)[C:5]=3[CH3:16])=[CH:9][CH:10]=2)[CH2:38][CH2:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 759941-BenzylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 22174864HCID 22174864, compound

Product 1

HCID 22174883HCID 22174883, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-[3,5-dimethyl-1-(4-pyridin-2-yl-pyrimidin-2-yl)-1H-pyrazol-4-yloxy]-benzaldehyde (0.545 g, 1.47 mmol) and 1-benzylpiperazine (0.310 g, 1.76 mmol) in dichloroethane (10 mL) was added sodium triacetoxyborohydride (0.436 g, 2.06 mmol). The reaction mixture was stirred at room temperature for 17 hours. The solution was diluted with methylene chloride (50 mL) and washed with saturated sodium hydrogencarbonate (2×30 mL) and brine (50 mL). The organic phase was dried (magnesium sulfate), filtered, and concentrated to afford a yellow oil. Flash chromatography over silica (2 M ammonia in methanol/methylene chloride) provided 0.183 g (23%) of the product as a white foam: 1H NMR (CDCl3) δ 8.94-8.93 (m, 1H), 8.75 (d, J=3.9 Hz, 1H), 8.46 (d, J=7.9 Hz, 1H), 8.25 (d, J=3.9 Hz, 1H), 7.90-7.87 (m, 1H), 7.46-7.43 (m, 1H), 7.31-7.21 (m, 7H), 6.89 (d, J=8.5 Hz, 2H), 3.52 (s, 2H), 3.47 (s, 2H), 2.68 (s, 3H), 2.48 (br s, 8H), 2.21 (s, 3H) ppm.

Workup

  1. washwashed with saturated sodium hydrogencarbonate (2×30 mL) and brine (50 mL)
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a yellow oil

Sources & evidence

ORD record
ord-285e8a7c1e1d48a58d3431d804d99e27
Source dataset
uspto-grants-2014_12
Patent number
US08921547B2

Reaction notes

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