Methanol → 3-(1H-Indol-4-yl)-1-methyl-3-piperidinol

HRID 1155682Notes

Reaction equation

HRID 1155682 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3([OH:16])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[BH4-].[Na+].O.[CH3:20]O>>[CH3:20][N:12]1[CH2:13][CH2:14][CH2:15][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH:3]=[CH:2][NH:1]3)([OH:16])[CH2:11]1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 12900685HCID 12900685, compound

Product 1

HCID 129006873-(1H-Indol-4-yl)-1-methyl-3-piperidinol

Procedure

5.8 g of a solution of 40% aqueous formal were added at 0° to -5° C. to a mixture of 13.3 g of 3-(1H-indol-4-yl)-3-piperidinol in 120 ml of methanol and after stirring the mixture for 15 minutes, 4.9 g of 95% sodium borohydride were added thereto. Water was added to the mixture which was then extracted with chloroform containing 20% of methanol. The organic phase was washed with water, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness and the 11.8 g of residue were crystallized from benzene to obtain 9 g of 1-methyl-3-(1H-indol-4-yl)-3-piperidinol melting 145° C.

Workup

  1. extractionwas then extracted with chloroform containing 20% of methanol
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe 11.8 g of residue were crystallized from benzene

Sources & evidence

ORD record
ord-5d3b65514a6448fba14a6ee5bbfb2a87
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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