Hydrochloric Acid → 5-(2-Amino-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester Hydrochloride

HRID 966543Notes

Reaction equation

HRID 966543 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][NH:22]C(OC(C)(C)C)=O)[CH:18]=2)[NH:13][C:12]=1[CH3:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:31]>O1CCOCC1>[ClH:31].[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][NH2:22])[CH:18]=2)[NH:13][C:12]=1[CH3:30])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10294893HCID 10294893, compound

Product 1

HCID 697397605-(2-Amino-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester HydrochlorideYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-(2-tert-butoxycarbonylamino ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (1.972 g, 4.827 mmol) in dioxane (25 mL) at room temperature was added aqueous HCl (3.0 mL, 37%). The resulting mixture was then stirred at ambient temperature for 22 hours. After this duration, the mixture was concentrated in vacuo. Trituration with acetone gave 1.48 g (89%) of the desired product as a white solid, mp 282-283° C.; MS (APCI+): m/z 309.0 (M+1).

Workup

  1. concentrationAfter this duration, the mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-75d092214cec4a89855105390f54a6ae
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

Loading…