HCID 13179835, compound → HCID 13179836, compound

HRID 543706Notes

Reaction equation

HRID 543706 reaction equation
CN(C)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH:13]2[CH2:18][CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14]2)[NH:6][CH:5]=1>CO>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)[NH:6][CH:5]=1

Participants

3

Reactant 1

HCID 13179835HCID 13179835, compound

Product 1

HCID 13179836HCID 13179836, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of 4.3 g of the product of Step A, 1.5 g of 10% palladized carbon and 300 ml of methanol was hydrogenated at 40° C. for one hour after which another 1.5 g of 10% palladized carbon were added. The hydrogenation was continued for another hour and the mixture was filtered. The filtrate was evaporated to dryness under reduced pressure at 50° C. to obtain 2.5 g of 3-methyl-4-(piperidin-3-yl)-1H-indole melting at 150° C. The said product was dissolved in 250 ml of ethyl acetate and then a solution of hydrogen chloride in ethyl acetate was added thereto at 0° to 5° C. until the mixture was acidic. The mixture was filtered and the product was washed with ethyl acetate, dried at 50° C. under reduced pressure and was crystallized from isopropanol to obtain 2.4 g of 3-methyl-4-(piperidin-3-yl)-1H-indole hydrochloride melting at 280° C.

Workup

  1. additionafter which another 1.5 g of 10% palladized carbon were added
  2. waitThe hydrogenation was continued for another hour
  3. filtrationthe mixture was filtered
  4. customThe filtrate was evaporated to dryness under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-8e67be3bf13a43cca0898bf358edd899
Source dataset
uspto-grants-1984_05
Patent number
US04447438

Reaction notes

Loading…