Sodium hydride → HCID 23463795, compound

HRID 444453Notes

Reaction equation

HRID 444453 reaction equation
[H-].[Na+].[C:3]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:23][CH2:22][NH:21][C:20]2=[O:24])[CH2:15][CH2:14]1)([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[O:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[O:31][CH2:32][CH2:33]Br>CN(C)C=O>[C:3]([N:13]1[CH2:14][CH2:15][CH:16]([N:19]2[CH2:23][CH2:22][N:21]([CH2:33][CH2:32][O:31][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][O:25]3)[C:20]2=[O:24])[CH2:17][CH2:18]1)([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 23463818Benzyl 4-(2-oxoimidazolidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 23463795HCID 23463795, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 1.35 g of sodium hydride in 70 ml of dimethylformamide and 14.2 g of 1-(1-carbobenzoxy-4-piperidyl)-imidazolidin-2-one is stirred at 80° C. for 4 hours. A solution of 11.7 g of 2-bromoethyl 2-tetrahydro-pyranyl ether in 30 ml of absolute dimethylformamide is then added dropwise in the course of 15 minutes. The mixture is stirred for a further 4 hours at 80° C. and is then evaporated under reduced pressure. The residue is freed from dimethylformamide which is still adhering, by treatment with toluene. The reaction product is dissolved in ethyl acetate, the solution is washed twice with, in each case, 50 ml of water and the ethyl acetate phase is dried over sodium sulphate and evaporated. The residual oil is chromatographed on 1.5 g of silica gel using a mixture of chloroform/methyl alcohol (95:5) as the eluant mixture. In this way, 1-(1-carbobenzoxy-4-piperidyl)-3-[2-(2-tetrahydropyranyloxy)-ethyl]-imidazolidin-2-one is obtained in the form of a slightly yellowish oil.

Workup

  1. stirringThe mixture is stirred for a further 4 hours at 80° C.
  2. customis then evaporated under reduced pressure
  3. dissolutionThe reaction product is dissolved in ethyl acetate
  4. washthe solution is washed twice with, in each case, 50 ml of water
  5. dry with materialthe ethyl acetate phase is dried over sodium sulphate
  6. customevaporated
  7. customThe residual oil is chromatographed on 1.5 g of silica gel using
  8. additiona mixture of chloroform/methyl alcohol (95:5) as the eluant mixture

Sources & evidence

ORD record
ord-3a4fcaec104045ad8ba594a775198339
Source dataset
uspto-grants-1981_04
Patent number
US04264599

Reaction notes

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