Methanol → N1-[3-(2-benzyl-4-chloro-phenoxy)-propyl]-N1-[bis-(4-methoxy-phenyl)-methyl]-ethane-1,2-diamine

HRID 2219211Notes

Reaction equation

HRID 2219211 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:14]1[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][N:20]([CH2:38][C:39]#[N:40])[CH:21]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CCOCC>[CH2:7]([C:14]1[CH:44]=[C:43]([Cl:45])[CH:42]=[CH:41][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][N:20]([CH:21]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:38][CH2:39][NH2:40])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 86610927{[3-(2-Benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amino}-acetonitrile

Product 1

HCID 58816148N1-[3-(2-benzyl-4-chloro-phenoxy)-propyl]-N1-[bis-(4-methoxy-phenyl)-methyl]-ethane-1,2-diamineYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (6.88 mL, 1N in THF) is added dropwise to a stirred solution of {[3-(2-benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amino}-acetonitrile (2.48 g, 4.58 mmol) in anhydrous THF (30 mL) at ambient temperature under nitrogen. The resultant mixture is allowed to stir at ambient temperature for 20 hours. The mixture is cooled to 0° C. before it is treated dropwise with CH3OH (5 mL), then followed by the addition of Et2O (30 mL) and saturated Rochelle's salt solution (80 mL). The two-layered mixture is allowed to stir vigorously at ambient temperature under nitrogen for 1 hour. Another 60 mL Et2O is added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica (gradient 0-4% 2N NH3/CH3OH in CH2Cl2) to give 1.92 g (3.52 mmol, 77% yield) of the title compound as oil. ESIMS: m/z 545 [(M+H)+, 35Cl]; 547 [(M+H)+, 37Cl].

Workup

  1. temperatureThe mixture is cooled to 0° C. before it
  2. stirringto stir vigorously at ambient temperature under nitrogen for 1 hour
  3. customThe organic layer is separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is chromatographed on silica (gradient 0-4% 2N NH3/CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-6a0a5f841a6f429c8ffe2af573126326
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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