Sodium hydride → HCID 86755691, compound

HRID 1872765Notes

Reaction equation

HRID 1872765 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3]1.[H-].[Na+].Cl[C:25]1[N:29]([CH2:30][CH2:31][O:32][CH2:33][CH3:34])[C:28]2[CH:35]=[CH:36][CH:37]=[CH:38][C:27]=2[N:26]=1>CN(C)C=O>[CH2:33]([O:32][CH2:31][CH2:30][N:29]1[C:28]2[CH:35]=[CH:36][CH:37]=[CH:38][C:27]=2[N:26]=[C:25]1[O:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:3]1)[CH3:34]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104893562-chloro-1-(2-ethoxyethyl)-1H-benzimidazoleHCID 86755692HCID 86755692, compound

Product 1

HCID 86755691HCID 86755691, compoundYield 118.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-1,1-dimethylethyl trans-4-hydroxy-2-(phenylmethyl)-1-piperidinecarboxylate (25.6 g) was dissolved in N,N-dimethylformamide (256 ml). Sodiumhydride (4.24 g) was added and the mixture was stirred at RT for 1.5 hours. 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazol (24.8 g) was added and the mixture was stirred at 70° C. for 18 hours. The solvent was evaporated, the residue taken up in water and CH2Cl2 and the layers were separated. The organic layer was dried, filtered and the solvent evaporated, yielding 50 g (100%) of (±)-1,1-dimethylethyl trans-4-[[1-(2-ethoxyethyl)-1H-benzimidazol-2-yl]oxy]-2-(phenylmethyl)-1-piperidine-carboxylate (interm 27).

Workup

  1. stirringthe mixture was stirred at 70° C. for 18 hours
  2. customThe solvent was evaporated
  3. customCH2Cl2 and the layers were separated
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-06ab1345182d4681a9e693a2fd9d4c16
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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