Ammonia → 4-(Piperidin-3-yl)-1H-indole

HRID 1155683Notes

Reaction equation

HRID 1155683 reaction equation
[Li].N.Cl.[NH:4]1[C:12]2[C:7](=[C:8]([C:13]3(O)[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.O1CCCC1>C(O)C>[NH:15]1[CH2:16][CH2:17][CH2:18][CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:7]=2[CH:6]=[CH:5][NH:4]3)[CH2:14]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 3028194LithiumHCID 12900686HCID 12900686, compound

Product 1

HCID 30677184-(Piperidin-3-yl)-1H-indoleYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

700 mg of lithium were added in small fractions over one hour at -40° C. to a mixture of 100 ml of ammonia, 1.2 g of 3-(1H-indol-4-yl)-3-piperidinol hydrochloride, 20 ml of tetrahydrofuran and 10 ml of anhydrous ethanol and the ammonia was evaporated at room temperature. The residue was taken up in 100 ml of water and the aqueous phase was extracted with chloroform containing 10% methanol. The organic phase was washed with water, dried and filtered. The filtrate was evaporated to dryness and the 950 mg of residue was chromatographed over silica gel. Elution with a 7-2-1-chloroform-methanol-triethylamine mixture yielded 665 mg of 4-(piperidin-3-yl)-1H-indole.

Workup

  1. customthe ammonia was evaporated at room temperature
  2. extractionthe aqueous phase was extracted with chloroform containing 10% methanol
  3. washThe organic phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe 950 mg of residue was chromatographed over silica gel
  8. washElution with a 7-2-1-chloroform-methanol-triethylamine mixture

Sources & evidence

ORD record
ord-878a87cde2ab4eaa863a2bca5ecc1717
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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