1,2-Dichloroethane → HCID 66649278, compound

HRID 469852Notes

Reaction equation

HRID 469852 reaction equation
O([BH-](OC(C)=O)OC(C)=O)C(C)=O.[Na+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[CH:23]1([O:28][C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[CH:32]=O)[CH2:27][CH2:26][CH2:25][CH2:24]1.ClCCCl>CC(O)=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][CH2:32][C:31]2[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:29]([O:28][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:30]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 78074-BromoanilineHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66649278HCID 66649278, compoundYield 118.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium triacetoxyl-borohydride (470 mg, 2.21 mmol) was added to a solution of 4-bromo-phenylamine (252 mg, 1.47 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (324 mg, 1.47 mmol) in 10 ml of 1,2-dichloroethtane (DCE), 0.5 ml of HOAc was added. The mixture was stirred overnight at room temperature, followed by addition of 15 ml of DCE. The organic phase was washed with water and dried over sodium sulfate. The solvent was removed by rotovap to give 656 mg of crude (4-bromo-phenyl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine. It was used for next step without further purification.

Workup

  1. additionwas added
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed by rotovap

Sources & evidence

ORD record
ord-7f7e1725551045ac82ebc69c91335169
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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