Acetic Acid → HCID 67134440, compound

HRID 2380976Notes

Reaction equation

HRID 2380976 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]1([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH:35](=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(O)(=O)C>ClCCl.O>[CH2:35]([NH:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][N:24]2[CH2:23][CH2:22][N:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:26][CH2:25]2)=[CH:33][CH:32]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23507360HCID 23507360, compound

Product 1

HCID 67134440HCID 67134440, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (282 mg, 1.34 mmol) was added in one portion to a stirred solution of 4-(4-phenyl-piperazin-1-yl methyl)-phenylamine, benzaldehyde (75 μl, 0.73 mmol) and acetic acid (43 μl, 0.73 mmol) in dry dichloromethane (6 ml) and the reaction was stirred for 16 hours at room temperature. Water was added and the organic layer separated then washed with brine and dried over magnesium sulfate. The solution was concentrated in vacuo and the crude residue purified by column chromatography (hexanes/ethyl acetate 1:1) to afford the title compound as a colourless solid (175 mg, 72%). HPLC retention time 7.53 min. Mass spectrum (ES+) m/z 358 (M+H).

Workup

  1. customthe organic layer separated
  2. washthen washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solution was concentrated in vacuo
  5. customthe crude residue purified by column chromatography (hexanes/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-3e86cbeb0cf24204b7e94866c2084546
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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