Isopropylamine → HCID 54397280, compound

HRID 1657467Notes

Reaction equation

HRID 1657467 reaction equation
[O:1]1[CH2:15][CH:2]1[CH2:3][O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[S:13][CH2:12][CH2:11][CH2:10]2.[CH:16]([NH2:19])([CH3:18])[CH3:17]>O1CCOCC1>[CH:16]([NH:19][CH2:15][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[S:13][CH2:12][CH2:11][CH2:10]2)([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 158404152-{[(3,4-Dihydro-2H-1-benzothiopyran-8-yl)oxy]methyl}oxirane

Product 1

HCID 54397280HCID 54397280, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6.9 g of crude 8-(2,3-epoxy propyloxy) thiochroman prepared as described above, 26 ml of isopropylamine and 53 ml of dry dioxan were refluxed for 20 hours. The reaction mixture was then evaporated to dryness, under vacuum. The residue was taken up with chloroform and diluted hydrochloric acid. The acid aqueous phase was made alkaline with an aqueous sodium hydroxide solution. There were obtained 4.6 g of dl 8-(3-isopropylamino-2-hydroxy propyloxy) thiochroman, melting (K) at 90° to 92°C, which recrystallized in cyclohexane, melted at 91 to 92°C. 3.9 g of this base were dissolved in 20 ml of ethanol and a solution of dry hydrochloric gas in ether was added.

Workup

  1. customprepared
  2. temperaturewere refluxed for 20 hours
  3. customThe reaction mixture was then evaporated to dryness, under vacuum

Sources & evidence

ORD record
ord-7f0e9068ad094496a15628de9562e8e9
Source dataset
uspto-grants-1976_06
Patent number
US03960891

Reaction notes

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