Propylamine → HCID 22270286, compound

HRID 488404Notes

Reaction equation

HRID 488404 reaction equation
Cl[CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6]2[CH:11]=[CH:12][C:13]([CH2:15][O:16][Si:17]([CH3:23])([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:5]=2[N:4]=1.[CH2:24]([NH2:27])[CH2:25][CH3:26]>C(#N)C>[CH2:24]([NH:27][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6]2[CH:11]=[CH:12][C:13]([CH2:15][O:16][Si:17]([CH3:23])([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:5]=2[N:4]=1)[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 22270285HCID 22270285, compound

Product 1

HCID 22270286HCID 22270286, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.0 g (5.6 mmole) of 1-{[2-(chloromethyl)-1-propylbenzimidazol-5-yl]methoxy}-1,1,2,2-tetramethyl-1-silapropane in 20 mL of anhydrous acetonitrile is treated with 10 mL of propylamine for 16 hr at room temperature. The solvent is removed in vacuo and the residue is partitioned between 30 mL of ethyl acetate and 10 mL of 1 N NaOH. The ethyl acetate layer is dried over anhydrous Na2SO4 and solvent removed in vacuo to afford 2.1 g (99%) of propyl({1-propyl-5-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]benzimidazol-2-yl}methyl)amine.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between 30 mL of ethyl acetate and 10 mL of 1 N NaOH
  3. dry with materialThe ethyl acetate layer is dried over anhydrous Na2SO4 and solvent
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-45aacbadc9f5465cac4ae748cb38417d
Source dataset
uspto-grants-2005_12
Patent number
US06972293B2

Reaction notes

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