Hydrochloric Acid → HCID 21071564, compound

HRID 1371874Notes

Reaction equation

HRID 1371874 reaction equation
[ClH:1].[C:2]1([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:19]=2[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][NH:13]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.CCOCC>[ClH:1].[C:2]1([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:19]=2[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][NH:13]3)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21071563HCID 21071563, compound

Product 1

HCID 21071564HCID 21071564, compound

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

Add a solution of HCl (4.6 mL of 4 M HCl in 1,4-dioxane) dropwise to a solution of 4-phenyltryptamine (3.33 g, 14.09 mmol) in EtOAc/Et2O to give a solid. Collect the solid by filtration and dry overnight in a vacuum oven at room temperature to give the title compound as an off white solid: 1H NMR (300 MHz, d6-DMSO): 2.54 (m, 4H), 6.82 (m, 1H), 7.14 (t, 1H), 7.27 (m, 1H), 7.41 (m, 5H), 7.68 (bs, 2H), 11.28 (bs, 1H); MS(ES+): m/z 237 (M+H)+, 220 (M-NH2)+; (ES−): m/z 235 (M−H)−; Analysis for C16H17ClN2; Calcd.; C, 70.4517; H, 6.2818; N, 10.2696; found; C, 70.26; H, 6.16; N, 10.20.

Workup

  1. customto give a solid
  2. customCollect the solid
  3. filtrationby filtration
  4. customdry overnight in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-e2815d9b48e44f49b06ee1570a395c8f
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

Loading…