Water → HCID 13423994, compound

HRID 1980253Notes

Reaction equation

HRID 1980253 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[OH:11].[CH2:12]([N:19]1[CH2:26][CH2:25][C:22]2([O:24][CH2:23]2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CN(C)C=O>[ClH:3].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[O:11][CH2:23][C:22]1([OH:24])[CH2:25][CH2:26][N:19]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 68992,6-DichlorophenolHCID 14797Potassium HydroxideHCID 892386-Benzyl-1-oxa-6-azaspiro(2,5)octane

Product 1

HCID 13423994HCID 13423994, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
76 °C

Procedure

The potassium salt of 2,6-dichlorophenol was formed by heating at 76° C. a mixture of 6.6 g (0.1 mole) of potassium hydroxide pellets (85%) and 16.3 (0.1 mole) of 2,6-dichlorophenol in 150 ml of dry dimethylformamide until a clear brown solution was obtained. The stirred solution was treated dropwise with 20.3 g (0.1 mole) of 6-benzyl-1-oxa-6-azaspiro[2.5]octane in 50 ml of dry dimethylformamide and heated at 80° C. for 120 hours. TLC (5% methyl benzene/silica gel G) indicated that the reaction was only 40% complete. The reaction mixture was treated with 4 volumes of water and the suspension extracted with three 100 ml portions of benzene. The extracts were combined, washed with 50 ml of 3N sodium hydroxide followed by three 50 ml portions of water, dried over magnesium sulfate and evaporated under reduced pressure to give 26.2 g of dark brown oil. The oil was chromatographed on a 500 g column of silica gel 60 and eluted with benzene followed by 1 to 10% acetone-benzene gradient. A small amount of 2,6-dichlorophenol was collected and discarded. The column was then eluted with a mixture of 1% methanol and 10% acetone in benzene. Fractions containing the product were combined and evaporated under reduced pressure to give 10.5 g of a yellow oil. The residual oil was converted to the hydrochloride salt in the usual way and recrystallized from acetone to give 5.2 g of product, m.p. 203°-205° C. with a phase change at 140°-153° C.

Workup

  1. customwas obtained
  2. temperatureheated at 80° C. for 120 hours
  3. extractionthe suspension extracted with three 100 ml portions of benzene
  4. washwashed with 50 ml of 3N sodium hydroxide
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6e6fdb725e37433a90ef1a61fff7ffcc
Source dataset
uspto-grants-1985_04
Patent number
US04508724

Reaction notes

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