Sodium Carbonate → HCID 2838208, compound

HRID 1676282Notes

Reaction equation

HRID 1676282 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Br:8][C:9]1[O:13][C:12]([CH:14]=O)=[CH:11][CH:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:8][C:9]1[O:13][C:12]([CH2:14][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 6003285-Bromofuran-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 2838208HCID 2838208, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottomed flask was charged with 1-methylpiperazine (2.02 mL, 18.2 mmol), 5-bromofuran-2-carbaldehyde (3.03 g, 17.3 mmol), and CH2Cl2 (30 mL). The reaction mixture was stirred for 30 minutes, and then sodium triacetoxy borohydride (4.77 g, 22.5 mmol) was added slowly over five minutes. The reaction mixture was stirred at room temperature for 4 hours, then poured into Na2CO3 (100 mL) and extracted with CH2Cl2 (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to provide the product (2.35 g, 50%) as an orange solid. LRMS (esi pos) m/e 260 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 hours
  2. extractionextracted with CH2Cl2 (2×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e58516562fec4203a2bbfb0e4afe955c
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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