Ammonia → 5-(1-H-Indol-3-yl)pentanoic acid amide

HRID 908940Notes

Reaction equation

HRID 908940 reaction equation
C(C[O:4][C:5](=O)[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)#N.[NH3:20]>O1CCCC1>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][C:5]([NH2:20])=[O:4])=[CH:11]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 673867685-(1H-Indol-3-yl)pentanoic acid cyanomethyl ester

Product 1

HCID 122769645-(1-H-Indol-3-yl)pentanoic acid amideYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(1H-indol-3-yl)pentanoic acid cyanomethyl ester (4.5 g, 17.5 mmol) in tetrahydrofuran (110 ml) was added to a 25 percent strength ammonia solution (80 ml) and the mixture was stirred at room temperature for 3 d. Working up of the mixture was carried out by phase separation and extraction of the aqueous phase with tetrahydrofuran (2×30 ml). The organic phases were combined, washed with saturated sodium chloride solution (50 ml), dried and concentrated. The residue was washed with water (2×10 ml) and ether (2×10 ml) and dried. The product remained as a colourless solid in a yield of 68% (2.56 g) with an m.p. of 134-139° C.

Workup

  1. customwas carried out by phase separation and extraction of the aqueous phase with tetrahydrofuran (2×30 ml)
  2. washwashed with saturated sodium chloride solution (50 ml)
  3. customdried
  4. concentrationconcentrated
  5. washThe residue was washed with water (2×10 ml) and ether (2×10 ml)
  6. customdried

Sources & evidence

ORD record
ord-24b93e919b5248969fd7d30b58bcebb1
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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