4-(Chloromethyl)-2-(cyclopentyloxy)-1-methoxybenzene → HCID 178463593, compound

HRID 1106974Notes

Reaction equation

HRID 1106974 reaction equation
[CH2:1]([NH:3][C:4]1[N:12]=[CH:11][NH:10][C:9]2[C:5]=1[N:6]=[C:7]([CH:13]([CH3:15])[CH3:14])[N:8]=2)[CH3:2].[CH:16]1([O:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=2[O:30][CH3:31])[CH2:25][Cl:26])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(#N)C>[ClH:26].[CH2:1]([NH:3][C:4]1[N:12]=[CH:11][N:10]([CH2:25][C:24]2[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:22]([O:21][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:23]=2)[C:9]2[C:5]=1[N:6]=[C:7]([CH:13]([CH3:14])[CH3:15])[N:8]=2)[CH3:2]

Participants

4

Reactant 2

HCID 109007664-(Chloromethyl)-2-(cyclopentyloxy)-1-methoxybenzeneHCID 178463603HCID 178463603, compound

Product 1

HCID 178463593HCID 178463593, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-ethylamino-8-isopropyl-3H-purine (7.52 g, 36.65 mmol) and 3-cyclopentyloxy-4-methoxybenzylchloride (10.59 g, 43.98 mmol) were dissolved in acetonitrile (30 ml) in a high pressure vessel and the resulting mixture heated are 120° C. for 24 hours. On cooling to room temperature a solid precipitated from the solution. The solvent was removed in vacuo, cold water (10 ml) and diethyl ether (100 ml) were added to the solid residue, the mixture stirred vigourously and then filtered. The filter cake was washed with ice-cold ethyl acetate (50 ml) and the solid obtained was oven dried in vacuo at 80° C. to give the title compound (9.51 g, 58%) as a slightly off-white solid. The combined filtrates and washings were concentrated in-vacuo, then water (5 ml) and diethyl ether (100 ml) added, and the mixture treated as before to give further title compound (0.718 g, 5%) as a white solid, m.p.=205-207° C. Combined yield 910.23 g, 63%). Tlc, SiO2 (dichloromethane:methanol, 10:1) Rf=0.49, detection U.V., Dragendorff's reagent.

Workup

  1. temperaturethe resulting mixture heated
  2. customprecipitated from the solution
  3. customThe solvent was removed in vacuo, cold water (10 ml) and diethyl ether (100 ml)
  4. additionwere added to the solid residue
  5. filtrationfiltered
  6. washThe filter cake was washed with ice-cold ethyl acetate (50 ml)
  7. customthe solid obtained
  8. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-77913975413d4014b0537ef94df55570
Source dataset
uspto-grants-2000_05
Patent number
US06057445

Reaction notes

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