Sodium borohydride → 2-(2'-Chloro-3-methyl-biphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propylamine

HRID 2194884Notes

Reaction equation

HRID 2194884 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][O:27][C:28]3[C:33]([Cl:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=3[Cl:36])=[CH:20][CH:19]=2)[C:15]#[N:16])=[C:10]([CH3:37])[CH:9]=1.[BH4-].[Na+]>CO.C1COCC1.[OH-].[Na+].CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][O:27][C:28]3[C:29]([Cl:36])=[CH:30][C:31]([CH3:35])=[CH:32][C:33]=3[Cl:34])=[CH:22][CH:23]=2)[CH2:15][NH2:16])=[C:10]([CH3:37])[CH:9]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 674478152-(2'-Chloro-3-methylbiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)-ethoxy]phenyl}propanenitrile

Product 1

HCID 251914962-(2'-Chloro-3-methyl-biphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-propylamine

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-(2′-chloro-3-methylbiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile from step 4 (1 eq.) in MeOH/THF (4:1; 0.08M) at room temperature was added cobaltous chloride hexahydrate (CoCl2.6H2O; 2 eq.) and then portionwise sodium borohydride (10 eq.). The final black mixture was stiffed for 12 h at room temperature, poured in aqueous NaOH (1N) and diluted with EtOAc. The precipitate was filtered-off on celite and the organic extract was washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel, eluting with CH2Cl2/MeOH(NH3 2M) 4%, afforded the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.52-7.48 (m, 1H); 7.40-7.25 (m, 6H); 7.11 (s, 2H); 6.98 (d, 2 H); 6.80 (d, 2H); 4.39-4.32 (m, 4H); 3.35 (m, 1H); 3.10 (m, 2H); 3.0-2.75 (m, 4H); 2.30 (s, 3 H); 2.20 (s, 3H).

Workup

  1. extractionthe organic extract
  2. washwas washed with saturated aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel
  7. washeluting with CH2Cl2/MeOH(NH3 2M) 4%

Sources & evidence

ORD record
ord-ff51f9e514884456aa23126f19fd4b74
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

Loading…