Acetic Acid → HCID 11703679, compound

HRID 1435557Notes

Reaction equation

HRID 1435557 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]3[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=3)[CH:27]=O)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1.[CH2:32]([NH:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:32]([N:39]([CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[C:24]([C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[NH:15][CH:16]=[CH:17]3)[CH:25]=1)[CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 660291,2-Ethanediamine, N1,N1-dimethyl-N2-(phenylmethyl)-HCID 516892Sodium BicarbonateHCID 41358793-(1H-indol-5-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 11703679HCID 11703679, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium triacetoxyborohydride (480 mg, 2.3 mmol) was added to a solution of 3-(1H-indol-5-yl)-benzaldehyde (250 mg, 1.1 mmol) and N′-benzyl-N,N-dimethyl-ethane-1,2-diamine (600 mg, 3.4 mmol) and acetic acid (204 mg, 3.4 mmol) in 8 mL of tetrahydrofuran. The mixture was stirred at ambient temperature overnight, and then it was diluted with ethyl acetate, and neutralized with the careful addition of saturated sodium bicarbonate solution. The layers were separated and the organic phase was treated with polystyrene supported isocyanate resin (1.49 mmol/g, 1.7 g) for 2 h. The mixture was filtered and the filtrate was washed with 1M sodium carbonate solution. The aqueous phase was extracted into ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated to leave 290 mg of the title compound. LC/MS (short method): retention time, 2.61 min; (M+H)=384.50.

Workup

  1. customThe layers were separated
  2. additionthe organic phase was treated with polystyrene
  3. customfor 2 h
  4. filtrationThe mixture was filtered
  5. washthe filtrate was washed with 1M sodium carbonate solution
  6. extractionThe aqueous phase was extracted into ethyl acetate
  7. dry with materialthe combined organic phases were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-efebb69552574c438f526672a796b3b5
Source dataset
uspto-grants-2009_11
Patent number
US07618650B2

Reaction notes

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