Acetic Acid → Ethyl 3-{4'-[(4-acetylpiperazin-1-yl)methyl]-2-(3-methoxypropoxy)biphenyl-4-yl}propanoate

HRID 1690615Notes

Reaction equation

HRID 1690615 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:5][CH:4]=1)=O.C(O)(=O)C.[C:32]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)(=[O:34])[CH3:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[C:32]([N:35]1[CH2:40][CH2:39][N:38]([CH2:1][C:3]2[CH:4]=[CH:5][C:6]([C:9]3[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=3[O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:7][CH:8]=2)[CH2:37][CH2:36]1)(=[O:34])[CH3:33]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 837951-AcetylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86633297Ethyl 3-[4'-formyl-2-(3-methoxypropoxy)biphenyl-4-yl]propanoate

Product 1

HCID 66906685Ethyl 3-{4'-[(4-acetylpiperazin-1-yl)methyl]-2-(3-methoxypropoxy)biphenyl-4-yl}propanoateYield 78.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Ethyl 3-[4′-formyl-2-(3-methoxypropoxy)biphenyl-4-yl]propanoate (1 g, 2.7 mmol) was dissolved in dichloroethane (20 mL). At 0° C., acetic acid (0.02 mL, 0.4 mmol) was added, followed by N-acetylpiperazine (0.38 g, 3 mmol) and sodium triacetoxyborohydride (0.86 g, 4 mmol) portionwise. The mixture was stirred at room temperature overnight. At 0° C., saturated aqueous sodium bicarbonate was added. The aqueous layer was extracted three times with dichloromethane. The combined organic layers were washed with brine and water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 1.02 g (78%) of the desired product as a brown oil.

Workup

  1. extractionThe aqueous layer was extracted three times with dichloromethane
  2. washThe combined organic layers were washed with brine and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-31f732a759514b65a74654383207441d
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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