Chloromethyl ethyl ether → HCID 20459110, compound

HRID 544390Notes

Reaction equation

HRID 544390 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:13]=2)=[N:5][C:4]([CH2:25][OH:26])=[N:3]1.[H-].[Na+].[CH2:29]([O:31][CH2:32]Cl)[CH3:30]>O1CCCC1.CN(C)C=O>[CH2:29]([O:31][CH2:32][O:26][CH2:25][C:4]1[N:5]=[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:13]=2)[N:2]([CH3:1])[N:3]=1)[CH3:30]

Participants

6

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 55473Loxtidine

Product 1

HCID 20459110HCID 20459110, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methyl-5-[[3-[3-(1-piperidinylmethyl)phenoxy]propyl]amino]-1H-1,2,4-triazole-3-methanol (3.6 g) in dry tetrahydrofuran (30 ml) and dry dimethylformamide (3 ml), was added to a suspension of an 80% dispersion of sodium hydride in mineral oil (0.31 g), in dry tetrahydrofuran (10 ml).The suspension was heated under reflux for 0.5 h. and cooled to room temperature. Chloromethyl ethyl ether (1.0 ml) was added dropwise, and thesuspension was heated at reflux for 1 h. The solvent was removed under reduced pressure, and the residual yellow oil was partitioned between aqueous sodium carbonate and ethyl acetate. The organic phase was chromatographed on silica using a mixture of dichloromethane:ethanol:0.880ammonia (100:8:1) to give an oil (0.7 g). This oil was distilled to give the title compound (0.44 g) as a pale yellow oil b.p. 220°/0.06 mm Hg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 0.5 h.
  3. temperaturethesuspension was heated
  4. temperatureat reflux for 1 h
  5. customThe solvent was removed under reduced pressure
  6. customthe residual yellow oil was partitioned between aqueous sodium carbonate and ethyl acetate
  7. customThe organic phase was chromatographed on silica using
  8. additiona mixture of dichloromethane

Sources & evidence

ORD record
ord-4bc7948440294950a38c13807808a81a
Source dataset
uspto-grants-1984_05
Patent number
US04450168

Reaction notes

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