4-Chlorobenzaldehyde → HCID 11510335, compound

HRID 1947076Notes

Reaction equation

HRID 1947076 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([N:11]2[CH2:15][CH:14]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH:13]([OH:22])[CH2:12]2)=[O:10])=[CH:5][CH:4]=1.[BH3-]C#N.[Na+].CC([O-])=O.[Na+].[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1>CO>[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][N:19]2[CH2:20][CH2:21][N:16]([CH:14]3[CH:13]([OH:22])[CH2:12][N:11]([C:9]([C:6]4[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=4)=[O:10])[CH2:15]3)[CH2:17][CH2:18]2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68513589HCID 68513589, compound

Product 1

HCID 11510335HCID 11510335, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-Chloro-phenyl)-(3-hydroxy-4-piperazin-1-yl-pyrrolidin-1-yl)-methanone hydrochloride (100 mg, 0.290 mmol), NaCNBH3 (20 mg, 0.319 mmol), NaOAc (23.8 mg, 0.29 mmol), 4-chloro-benzaldehyde (42.8 mg, 0.30 mmol) were added to methanol (3 mL). The reaction mixture was stirred in room temperature for over night. The mixture was concentrated. K2CO3 and Ethyl acetate were added to the residue. The organic phase was washed with brine, dried over Na2SO4, and concentrated. The crude was purified by column chromatography to give 70 mg of desired product as an oil (56% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. additionK2CO3 and Ethyl acetate were added to the residue
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-a5fbdb98111749d6975e3e3878534d66
Source dataset
uspto-grants-2013_03
Patent number
US08399455B2

Reaction notes

Loading…