5-[2-(Dibenzylamino)-1-hydroxyethyl]-indole-7-carboxamide → 5-(1-hydroxy-2-aminoethyl)-1H-indole-7-carboxamide

HRID 1731600Notes

Reaction equation

HRID 1731600 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][CH:10]([C:12]1[CH:13]=[C:14]2[C:18](=[C:19]([C:21]([NH2:23])=[O:22])[CH:20]=1)[NH:17][CH:16]=[CH:15]2)[OH:11])C1C=CC=CC=1>CO.[Pd]>[NH2:8][CH2:9][CH:10]([C:12]1[CH:13]=[C:14]2[C:18](=[C:19]([C:21]([NH2:23])=[O:22])[CH:20]=1)[NH:17][CH:16]=[CH:15]2)[OH:11]

Participants

4

Reactant 1

HCID 134722955-[2-(Dibenzylamino)-1-hydroxyethyl]-indole-7-carboxamide

Product 1

HCID 1279335-(1-hydroxy-2-aminoethyl)-1H-indole-7-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-[2-(dibenzylamino)-1-hydroxyethyl]-indole-7-carboxamide (119.7 mg, 0.3 mmol, described above) was hydrogenated for 28 hours at atmospheric pressure and room temperature in dry methanol (12.0 mL) containing 10% palladium on carbon. The mixture was filtered and the filtrate was evaporated. Crystallization from an ethyl acetate-diethyl ether mixture gave 5-(2-amino-1-hydroxyethyl)indole-7-carboxamide: mp 88°-90° C.; and NMR (DMSO-d6) δ 2.70 (d, 2H), 2.80-3.60 (br s, 5H), 4.50 (t, 1H), 6.40 (m, 1H), 7.00-7.70 (m, 3H) and 10.75 (br s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customCrystallization from an ethyl acetate-diethyl ether mixture

Sources & evidence

ORD record
ord-eb303e2f448d45af9ea85d8b8edee0d3
Source dataset
uspto-grants-1986_11
Patent number
US04622399

Reaction notes

Loading…