Benzene → HCID 20320085, compound

HRID 866656Notes

Reaction equation

HRID 866656 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:4]1.[C:18]1([CH:25]=[CH:24][C:22]([OH:23])=[CH:21][CH:20]=1)O.[CH:26]1[CH:31]=CC=CC=1.C[OH:33].CC[O:36][CH2:37][CH3:38]>>[O:33]1[C:21]2[CH:20]=[CH:18][CH:25]=[CH:24][C:22]=2[O:23][CH2:26][CH:31]1[CH:37]([OH:36])[CH2:38][N:15]1[CH2:16][CH2:17][CH:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH3:2])[CH:4]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 5

HCID 241BenzeneHCID 785HydroquinoneHCID 887MethanolHCID 3283Diethyl EtherHCID 203200861H-Indole, 1-methyl-3-(4-piperidinyl)-, hydrochloride (1:1)

Product 1

HCID 20320085HCID 20320085, compound

Procedure

A mixture of 12.5 g of 4-(1-methyl-[1H]-indol-3-yl)-piperidine hydrochloride, 10.7 g of 2,3-dihydro-2-oxiranyl-1,4-benzodioxin, 0.1 g of hydroquinone, 120 ml of benzene and 20 ml of methanol was refluxed with stirring under nitrogen for 2 hours and was then cooled and poured into 200 ml of ether to effect crystallization. The mixture was treated with 100 ml of aqueous 5% sodium bicarbonate solution and the organic phase was decanted. The aqueous phase was extracted with methylene chloride and the combined organic phases were washed with water until the wash water was neutral, dried, decolorized with activated carbon and evaporated to dryness. The 20 g of brown oil residue was chromatographed over silica gel and was eluted with a 95-5 methylene chloride-methanol mixture. Evaporation of the eluates was followed by crystallization of the residue from ethanol to obtain 8.6 g of α-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-(1-methyl-[1H]-indol-3-yl)-1-piperidine-ethanol after a second crystallization from ethanol in the form of a white solid melting at 155° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewas then cooled
  3. customcrystallization
  4. additionThe mixture was treated with 100 ml of aqueous 5% sodium bicarbonate solution
  5. customthe organic phase was decanted
  6. extractionThe aqueous phase was extracted with methylene chloride
  7. washthe combined organic phases were washed with water until the wash water
  8. customdried
  9. customevaporated to dryness
  10. customThe 20 g of brown oil residue was chromatographed over silica gel
  11. washwas eluted with a 95-5 methylene chloride-methanol mixture
  12. customEvaporation of the eluates
  13. customwas followed by crystallization of the residue from ethanol

Sources & evidence

ORD record
ord-355e08e4eabb47f6b5e424585adb826a
Source dataset
uspto-grants-1978_07
Patent number
US04100291

Reaction notes

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