HCID 21510694, compound → 3-[2-(4-Hydroxy-4-phenylpiperidin-1-yl)ethyl]-1H-indol-5-ol

HRID 1576484Notes

Reaction equation

HRID 1576484 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][C:23]([OH:32])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:22][CH2:21]1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][C:23]([OH:32])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:24][CH2:25]1

Participants

4

Reactant 1

HCID 21510694HCID 21510694, compound

Product 1

HCID 215107113-[2-(4-Hydroxy-4-phenylpiperidin-1-yl)ethyl]-1H-indol-5-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10 g. of 5-benzyloxy-3-[2-(4-hydroxy-4-phenylpiperidinyl)ethyl]indole in 10 ml. of ethanol was shaken on the Parr apparatus at room temperature at an initial pressure of 50 p.s.i., using a 10% palladium on charcoal catalyst. After debenzylation was complete the solution was filtered and the catalyst washed thoroughly with three 100 ml. portions of hot ethanol. Concentration of the original filtrate gave 3 g. of an oil which solidified and was recrystallized from ethyl acetate-methanol to give 1.85 g. of material which melted at 150° C., resolidified and melted again at 235°-240° C. The combined alcohol washes on concentration gave 4 g. of a white solid which after recrystallization from ethyl acetate-methanol gave 3.4 g. of material which melted at 150° C., recrystallized and melted again at 235°-240° C. A nuclear magnetic resonance spectrum indicated the above solids to be solvated with methanol. A sample was dried in vacuo at 110° for 24 hours; the dried sample melted at 238°-240° C.

Workup

  1. filtrationwas filtered
  2. washthe catalyst washed thoroughly with three 100 ml
  3. customConcentration of the original filtrate gave 3 g
  4. customwas recrystallized from ethyl acetate-methanol
  5. customto give 1.85 g
  6. custommelted again at 235°-240° C
  7. concentrationThe combined alcohol washes on concentration
  8. customgave 4 g
  9. customof a white solid which after recrystallization from ethyl acetate-methanol
  10. customgave 3.4 g
  11. customof material which melted at 150° C., recrystallized
  12. custommelted again at 235°-240° C
  13. customA sample was dried in vacuo at 110° for 24 hours

Sources & evidence

ORD record
ord-45258fb7933a40fbb7b1540f2315306e
Source dataset
uspto-grants-1976_09
Patent number
USRE028973

Reaction notes

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