1,2-Dichloroethane → HCID 67130576, compound

HRID 2380961Notes

Reaction equation

HRID 2380961 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Cl[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:49]CCCl>>[Cl:49][C:30]1[CH:29]=[CH:28][C:25]([CH2:26][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:12][CH2:11]3)=[O:9])=[CH:6][CH:7]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 114773-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 12932882(4-Aminophenyl)(4-phenylpiperazin-1-yl)methanone

Product 1

HCID 67130576HCID 67130576, compoundYield 25%

Procedure

To a stirred solution of (4-amino-phenyl)-(4-phenyl-piperazin-1-yl)-methanone (200 mg, 0.71 mmol) in 1,2-dichloroethane (4 ml) at 0° C. was added 3-chlorobenzaldehyde (99.7 mg, 0.71 mmol). Sodium triacetoxy borohydride (210 mg, 0.99 mmol) and acetic acid (40.6 μl, 0.71 mmol) were added and the reaction was stirred at room temperature under nitrogen overnight. The reaction was quenched with the addition of sodium hydroxide (aq.) (pH8) and extracted with diethyl ether (3×20 ml). The organic extracts were combined, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound as a yellow solid (72 mg, 25% yield). HPLC retention time 7.5 min. Mass spectrum (ES+) m/z 406 (M+H).

Workup

  1. customThe reaction was quenched with the addition of sodium hydroxide (aq.) (pH8)
  2. extractionextracted with diethyl ether (3×20 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-179fa51d375149e885fef553c0829395
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

Loading…